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卡托普利

卡托普利用途

Captopril是血管紧张素转化酶(ACE)抑制剂。
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卡托普利名称

[ CAS 号 ]:
62571-86-2

[ 中文名 ]:
甲巯丙脯酸

[ 英文名 ]:
Captopril

[中文别名 ]:

[英文别名 ]:

卡托普利生物活性

[ 描述 ]:

Captopril是血管紧张素转化酶(ACE)抑制剂。

[ 相关类别 ]:

信号通路 >> 代谢酶/蛋白酶 >> 血管紧张素转换酶(ACE)
研究领域 >> 神经疾病

[溶解度]

体外:

在DMSO中10mM


[储备液]

1 mM 4.6021 mL 23.0107 mL 46.0214 mL
5 mM 0.9204 mL 4.6021 mL 9.2043 mL
10 mM 0.4602 mL 2.3011 mL 4.6021 mL

[存储]

粉末 -20℃下 3年
4℃下 2年
在溶剂中 -80℃下 6个月
-20℃下 1个月

[运输]

室温;可能会有所不同

[SMILES]

O=C(O)[C@H]1N(C([C@H](C)CS)=O)CCC1

[参考文献]

[1]. Tzakos, A.G., et al., The molecular basis for the selection of captopril cis and trans conformations by angiotensin I converting enzyme. Bioorg Med Chem Lett, 2006. 16(19): p. 5084-7.

[2]. Song, J.C. and C.M. White, Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet, 2002. 41(3): p. 207-24.


[相关活性小分子]

血管紧张素1-7 | 马来酸依那普利 | 培哚普利 | 赖诺普利 | Phosphoramidon Disodium | 群多普利 | 福辛普利钠 | 盐酸喹那普利 | 雷米普利 | 西拉普利 | 依那普利那二水 | 奥马曲拉 | 盐酸替莫普利 | 血啡-7 | 盐酸莫昔普利

[相关文档]

*以上文档由Medchemexpress提供,仅用于科学研究参考。

卡托普利物理化学性质

[ 密度 ]:
1.3±0.1 g/cm3

[ 沸点 ]:
427.0±40.0 °C at 760 mmHg

[ 熔点 ]:
104-108 °C(lit.)

[ 分子式 ]:
C9H15NO3S

[ 分子量 ]:
217.285

[ 闪点 ]:
212.1±27.3 °C

[ 精确质量 ]:
217.077271

[ PSA ]:
96.41000

[ LogP ]:
0.27

[ 外观性状 ]:
白色至灰白色结晶粉末

[ 蒸汽压 ]:
0.0±2.2 mmHg at 25°C

[ 折射率 ]:
1.551

[ 水溶解性 ]:
soluble

卡托普利MSDS

卡托普利毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UY0550000
CHEMICAL NAME :
1-Pyrrolidinecarboxylic acid, 1-(D-3-mercapto-2-methyl-1-propionyl)-, L-(S,S)-
CAS REGISTRY NUMBER :
62571-86-2
LAST UPDATED :
199609
DATA ITEMS CITED :
33
MOLECULAR FORMULA :
C9-H15-N-O3-S
MOLECULAR WEIGHT :
217.31
WISWESSER LINE NOTATION :
T5NTJ AVY1&1SH BVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Vascular - BP lowering not characterized in autonomic section
REFERENCE :
AEMED3 Annals of Emergency Medicine. (American College of Emergency Physicians, 1125 Executive Circle, Irving, TX 75038) Volume(issue)/page/year: 20,1125,1991
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JTCTDW Journal of Toxicology, Clinical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.19- 1982- Volume(issue)/page/year: 28,379,1990
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
4 mg/kg/8D-I
TOXIC EFFECTS :
Behavioral - toxic psychosis
REFERENCE :
AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 142,270,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
239 mg/kg/6W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Taste) - change in function Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - normocytic anemia
REFERENCE :
AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 71,493,1981
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
2500 ug/kg/3D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume decreased Kidney, Ureter, Bladder - other changes
REFERENCE :
PGMJAO Postgraduate Medical Journal. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1925- Volume(issue)/page/year: 60,561,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
2679 ug/kg/5D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
IJMDAI Israel Journal of Medical Sciences. (POB 1435, Jerusalem 91013, Israel) V.1- 1965- Volume(issue)/page/year: 21,892,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
7143 ug/kg/2D-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 294,91,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
12500 ug/kg/25D-I
TOXIC EFFECTS :
Blood - other hemolysis with or without anemia
REFERENCE :
CMAJAX Canadian Medical Association Journal. (Canadian Medical Assoc., POB 8650, Ottawa, ON K1G 0G8, Canada) V.1- 1911- Volume(issue)/page/year: 129,525,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
14 mg/kg/2W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Biochemical - Metabolism (Intermediary) - other
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 104,126,1986
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1500 ug/kg/7W
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 94,58,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
10 mg/kg/10D-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 294,91,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
87 mg/kg/18W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes primarily in glomeruli Kidney, Ureter, Bladder - proteinuria Kidney, Ureter, Bladder - hematuria
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 112,550,1990
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
2680 ug/kg/5D-I
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - changes in potassium
REFERENCE :
SMJOAV Southern Medical Journal. (Southern Medical Assoc., POB 2446, Birmingham, AL 35205) V.1- 1908- Volume(issue)/page/year: 86,1269,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4245 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,297,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 24,2439,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
554 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,297,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 22,212,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>2400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 24,2439,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
663 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,297,1983
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>600 mg/kg
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting
REFERENCE :
44XQA7 "Captopril and Hypertension, Collection of Papers presented at a Symposium, Princeton, N.J., 1979?," Case, David B., et al. eds., New York, Plenum Publishing, 1980 Volume(issue)/page/year: -,137,1980
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
>1500 mg/kg
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting
REFERENCE :
44XQA7 "Captopril and Hypertension, Collection of Papers presented at a Symposium, Princeton, N.J., 1979?," Case, David B., et al. eds., New York, Plenum Publishing, 1980 Volume(issue)/page/year: -,137,1980 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
45 gm/kg/13W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in bladder weight Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 45,15,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3 gm/kg/30D-I
TOXIC EFFECTS :
Cardiac - changes in heart weight Liver - changes in liver weight Blood - changes in other cell count (unspecified)
REFERENCE :
JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 6(Suppl 2),189,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
36500 mg/kg/1Y-C
TOXIC EFFECTS :
Cardiac - changes in heart weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count
REFERENCE :
JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 6(Suppl 2),215,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
9100 mg/kg/91D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 6(Suppl 2),247,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
6300 mg/kg/28D-I
TOXIC EFFECTS :
Blood - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes
REFERENCE :
44XQA7 "Captopril and Hypertension, Collection of Papers presented at a Symposium, Princeton, N.J., 1979?," Case, David B., et al. eds., New York, Plenum Publishing, 1980 Volume(issue)/page/year: -,137,1980 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
228 mg/kg
SEX/DURATION :
male 43 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - breast development
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 296,1262,1988
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
48 gm/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 13,7041,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
RCOCB8 Research Communications in Chemical Pathology and Pharmacology. (PJD Pub. Ltd., P.O. Box 966, Westbury, NY 11590) V.1- 1970- Volume(issue)/page/year: 73,221,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
RCOCB8 Research Communications in Chemical Pathology and Pharmacology. (PJD Pub. Ltd., P.O. Box 966, Westbury, NY 11590) V.1- 1970- Volume(issue)/page/year: 73,221,1991
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
40 mg/kg
SEX/DURATION :
female 15-30 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 170,378,1982
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8250 ug/kg
SEX/DURATION :
female 24-28 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,1256,1980 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4863 No. of Facilities: 27 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 642 (estimated) No. of Female Employees: 346 (estimated)
点击显示

卡托普利安全信息

[ 符号 ]:

GHS07, GHS08

[ 信号词 ]:
Warning

[ 危害声明 ]:
H317-H361

[ 警示性声明 ]:
P280

[ 个人防护装备 ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ 危害码 (欧洲) ]:
Xi:Irritant

[ 风险声明 (欧洲) ]:
R36/37/38

[ 安全声明 (欧洲) ]:
S36/37-S37/39-S26

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
2

[ RTECS号 ]:
UY0550000

[ 海关编码 ]:
2933990090

卡托普利合成路线

卡托普利上下游产品

卡托普利制备

(一)由L-脯氨酸经异丁烯缩合、苄氧基羰酰氯酯化、氢气氢化、3-乙酰硫代-2-甲基丙酸缩合、双环己胺成盐、脱盐、水解而得。
(二)1:230g L-脯氨酸溶于1L水和400ml 5mol/L氢氧化钠所成的溶液,用冰浴冷却,在剧烈搅拌下,半小时内分5批加入460ml 5mol/L氢氧化钠和340ml氯甲酸苄酯。加毕在室温下搅拌1h,反应液用乙醚萃取2次后,用浓盐酸酸化。沉淀过滤,干燥,得442g N-苄基羰基-L-脯氨酸,熔点78-80℃。
180gN-苄基羰基-L-脯氨酸溶于300ml二氯甲烷,800ml液体异丁烯和7.2ml浓硫酸所成的溶液,在压力容器中震荡72h。减压后,蒸去异丁烯,剩余液依次用5%碳酸钠及水洗,用无水硫酸镁干燥,减压浓缩至干,得205g N-苄基羰基-L-脯氨酸叔丁酯。
205g N-苄基羰基-L-脯氨酸叔丁酯溶于1.2 L无水乙醇,在常压下以10%钯-炭为催化剂,加氢氢化直至逸出的氢气中仅有痕量的二氧化碳(约24h)。过滤除去催化剂,滤液在4.0kPa下浓缩,剩余物真空蒸馏,得到L-脯氨酸叔丁酯,沸点50~51℃/133Pa。
5.1g L-脯氨酸叔丁酯溶于40ml二氯甲烷,搅拌并用冰浴冷却。加入15ml DCC(二环己基碳化二亚胺),随后立刻加入4.9g 3-乙酰巯基-2-甲基丙酸溶于5ml二氯甲烷所成的溶液。在冰浴上搅拌15min后,再在室温下搅拌16h,过滤除去沉淀,滤液减压浓缩至干。剩余物溶于醋酸乙酯,水洗至中性,无水硫酸镁干燥,过滤,减压浓缩至干。剩余物即为N-(3-乙酰巯基-2-甲基丙酰基)-L-脯氨基叔丁酯,用柱层析(硅胶-氯仿)提纯后得7.9g。
往55ml苯甲醚和110ml三氟乙酸的混合溶液中,加入7.8g N-(3-乙酰巯基-2-甲基丙酰基)-L-脯氨酸叔丁酯,在室温下放置1h。减压蒸去溶剂,剩余物用乙醚-己烷沉淀数次。沉淀物(6.8g,消旋体)溶于40ml乙腈,加入4.5ml二环己胺,其中只有(S,S)异构体可和二环己胺成盐。过滤出结晶的盐,并在新蒸馏过的乙腈中沸腾,然后冷至室温,过滤,得到3.8g的(S,S)L-脯氨酸衍生物的二环己胺盐,熔点187~188℃。用丙醇重结晶后,[α]D-67°(C=1.4,乙醇)。该盐悬浮于5%硫酸氢钾和醋酸乙酯的混合溶液。分出的有机层水洗,并浓缩至干,剩余物用醋酸乙酯-己烷结晶,得光学活性的(S,S)-N-(3-乙酰巯基-2-D-甲基丙酰基)-1-脯氨酸,熔点83~85℃。
0.85g上述得到的光学活性的脯氨酸衍生物溶于5.5mol/L氨的甲醇溶液,在室温下保持2h,减压蒸去溶剂,剩余物溶于水,用酸型离子交换树脂(Dowex50,分析级)进行层析,展开液为水。收集巯醇试验现阳性的流出液,冷冰干燥。剩余物用丙酮-己烷结晶,得0.3g的卡托普利,熔点103~104℃。


方法2:α-甲基丙烯酸和硫代乙酸加成,得到α-甲基-β-乙酰硫基乙酸,再用氯化亚砜氯化成酰氯后,直接和脯氨酸在氢氧化钠(作为缚酸剂)的作用下,得到N-(3-乙酰巯基-2-甲基丙酰基)-L-脯氨酸,此是消旋体,和方法1一样,用二环己胺成盐进行光学拆分,得到(S,S)体,然后氨解脱去乙酰基,即得卡托普利。


方法3:2-甲基丙烯酸溶于氯仿,在-10℃和搅拌下,通入理论量的溴化氢0℃静置过夜。浓缩,收集81.5~84℃/670Pa的馏分,得3-溴-2-甲基丙酸,收率90.9%~93.1%。往3-溴-2-甲基丙酸中,滴加氯化亚砜,升至70℃搅拌。排除残气后,收集41~43℃/1.2kPa的馏分,得3-溴-2-甲基丙酰氯,收率89.5%~90.3%。在-2℃和搅拌下,往8%氢氧化钠和L-且甫氨酸的溶液中,滴加3-溴-2-甲基丙酰氯。滴完搅拌。冷却,用浓盐酸调至Ph=1~2,乙酸乙酯提取,干燥,过滤。搅拌下滴入二环己胺,然后置冰柜中冷却,抽滤,干燥,异丙醇重结晶,得化合物(I)的二环己胺盐,收率47.1%~48.3%。将其溶于10%硫酸氢钾,加入乙酸乙酯,搅拌,用乙酸乙酯提取,干燥,过滤,蒸干,用乙酸乙酯-正己烷重结晶,得有光学活性的化合物(I),收率85.5%~88.6%,[α]D20-94°~-95.4°。将化合物(I)、氢氧化钠水溶液和三硫代碳钠,在50℃搅拌。冷至室温,过滤,乙酸乙酯提取,干燥,过滤,浓缩,用乙酸乙酯重结晶,得卡托普利,收率65.9%,熔点104~107℃,[α]D20-127°(C=2.0,乙醇)。

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