Protected meropenem

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Names

[ CAS No. ]:
96036-02-1

[ Name ]:
Protected meropenem

[Synonym ]:
1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester, (4R,5S,6S)-
p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate
MFCD08703333
(4R,5S,6S)-p-nitrobenzyl 3-<(3S,5S)-(5-dimethylaminocarbonyl-1-p-nitrobenzyloxycarbonyl)pyrrolidin-3-yl>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
4-Nitrobenzyl (4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)-1-{[(4-nitrobenzyl)oxy]carbonyl}-3-pyrrolidinyl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
4-nitrobenzyl (4R,5S,6S)-3-(((3S,5S)-5-[(dimethylamino)carbonyl]-1-[(4-nitrophenoxy)carbonxyl]pyrrolidin-3-yl)thio)-6-[(1R)-1-hydorxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
p-nitrobenzyl (4R,5S,6S)-3-[[(3S,5S)-1-(p-nitrobenzyloxycarbonyl)-5-(dimethylaminocarbonyl)-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
3-[[5-[dimethylamino(oxo)methyl]-1-[(4-nitrophenyl)methoxy-oxomethyl]-2-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester
4-nitrobenzyl (4R,5S,6S)-3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-1-[[(4-nitrobenzyl)oxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
(4-nitrophenyl)methyl 3-[5-(dimethylcarbamoyl)-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-2-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxidanylidene-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
(4R,5S,6S)-(p-nitrobenzyl) 3-[[(3S,5S)-1-(p-nitrobenzyloxycarbonyl)-5-(dimethylaminocarbonyl)-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
900.3±65.0 °C at 760 mmHg

[ Melting Point ]:
150-153ºC (dec.)

[ Molecular Formula ]:
C32H35N5O11S

[ Molecular Weight ]:
697.712

[ Flash Point ]:
498.3±34.3 °C

[ Exact Mass ]:
697.205383

[ PSA ]:
233.63000

[ LogP ]:
-0.64

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.673

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • Side chain for meropenem
  • Citric acid monohydrate
  • 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate
  • 2-Azetidineacetic acid, 3-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-α-methyl-4-oxo-, phenylmethyl ester, [2S-[2α(S*),3β(S*)]]

DownStream

  • Meropenem

Related Compounds

  • protected amine BIB
  • protected dipeptide
  • Protected Imipenem
  • Cyclo[L-α-aspartyl-O-(1,1-dimethylethyl)-D-tyrosyl-L-lysyl-N5-[[[(2,3-dihydro-2,2,4,6,7-pentamethyl-5-benzofuranyl)sulfonyl]amino]iminomethyl]-L-ornithylglycyl], 1,1-dimethylethyl ester
  • Fmoc-protected threonine methyl ester
  • N-benzoyl-5'-O-(bis(4-methoxyphenyl)phenylmethyl)-P-(2-chlorophenyl)-2'-deoxyadenylyl-(3'->5')-N-benzoyl-2'-deoxy-3'-cytidylic acid, 2-chlorophenyl 2-cyanoethyl ester