Synthesis of. beta.-lactam antibiotics by the sulfeno-cycloamination

M Ihara, Y Haga, M Yonekura, T Ohsawa…

Index: Ihara; Haga; Yonekura; et al. Journal of the American Chemical Society, 1983 , vol. 105, # 25 p. 7345 - 7352

Full Text: HTML

Citation Number: 32

Abstract

Abstract: A novel efficient P-lactam synthesis was achieved by two successive processes (sulfeno-cycloamination), addition of phenylsulfenyl chloride to ru,@-unsaturated amides followed by base treatment. Key synthetic intermediates of monobactams and nocardicin derivatives were obtained via this method. Construction of the I-carbapenam ring system by the sulfenocycloamination is also described.

 Related Synthetic Route
N-(4-METHOXY-PHENYL)-2-METHYL-ACRYLAMIDE Structure

7274-71-7

N-(4-METHOXY-PH...

~%

1-(4-methoxyphenyl)azetidine-2,3-dione Structure

87568-43-2

1-(4-methoxyphe...

1-(4-methoxyphenyl)-3-methyl-3-phenylsulfanylazetidin-2-one Structure

87568-30-7

1-(4-methoxyphe...

~%

1-(4-methoxyphenyl)azetidine-2,3-dione Structure

87568-43-2

1-(4-methoxyphe...

3-(benzenesulfinyl)-1-(4-methoxyphenyl)-3-methylazetidin-2-one Structure

87568-42-1

3-(benzenesulfi...

~%

1-(4-methoxyphenyl)azetidine-2,3-dione Structure

87568-43-2

1-(4-methoxyphe...

1-(4-methoxyphenyl)-3-methylideneazetidin-2-one Structure

69193-56-2

1-(4-methoxyphe...

~%

1-(4-methoxyphenyl)azetidine-2,3-dione Structure

87568-43-2

1-(4-methoxyphe...

Benzyl carbamate Structure

621-84-1

Benzyl carbamate

Pyruvic acid Structure

127-17-3

Pyruvic acid

~46%

z-dehydro-ala-oh Structure

39692-63-2

z-dehydro-ala-oh

4-but-3-enylazetidin-2-one Structure

74373-13-0

4-but-3-enylaze...

~%

4-(4-chloro-3-phenylsulfanylbutyl)azetidin-2-one Structure

74373-19-6

4-(4-chloro-3-p...

4-but-3-enylazetidin-2-one Structure

74373-13-0

4-but-3-enylaze...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

4-(4-chloro-3-phenylsulfanylbutyl)azetidin-2-one Structure

74373-19-6

4-(4-chloro-3-p...

4-(3-chloro-4-phenylsulfanylbutyl)azetidin-2-one Structure

87568-56-7

4-(3-chloro-4-p...

4-but-3-enyl-1-[tert-butyl(dimethyl)silyl]azetidin-2-one Structure

109975-76-0

4-but-3-enyl-1-...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

4-(4-chloro-3-phenylsulfanylbutyl)azetidin-2-one Structure

74373-19-6

4-(4-chloro-3-p...

4-(3-chloro-4-phenylsulfanylbutyl)azetidin-2-one Structure

87568-56-7

4-(3-chloro-4-p...

1-(4-methoxyphenyl)azetidine-2,3-dione Structure

87568-43-2

1-(4-methoxyphe...

~61%

3-hydroxyimino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-44-3

3-hydroxyimino-...

1-(4-methoxyphenyl)-3-methylideneazetidin-2-one Structure

69193-56-2

1-(4-methoxyphe...

~%

3-hydroxyimino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-44-3

3-hydroxyimino-...

N-(4-METHOXY-PHENYL)-2-METHYL-ACRYLAMIDE Structure

7274-71-7

N-(4-METHOXY-PH...

~%

3-hydroxyimino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-44-3

3-hydroxyimino-...

1-(4-methoxyphenyl)-3-methyl-3-phenylsulfanylazetidin-2-one Structure

87568-30-7

1-(4-methoxyphe...

~%

3-hydroxyimino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-44-3

3-hydroxyimino-...

3-(benzenesulfinyl)-1-(4-methoxyphenyl)-3-methylazetidin-2-one Structure

87568-42-1

3-(benzenesulfi...

~%

3-hydroxyimino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-44-3

3-hydroxyimino-...

3-hydroxyimino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-44-3

3-hydroxyimino-...

~75%

3-amino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-45-4

3-amino-1-(4-me...

1-(4-methoxyphenyl)-3-methylideneazetidin-2-one Structure

69193-56-2

1-(4-methoxyphe...

~%

3-amino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-45-4

3-amino-1-(4-me...

N-(4-METHOXY-PHENYL)-2-METHYL-ACRYLAMIDE Structure

7274-71-7

N-(4-METHOXY-PH...

~%

3-amino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-45-4

3-amino-1-(4-me...

1-(4-methoxyphenyl)azetidine-2,3-dione Structure

87568-43-2

1-(4-methoxyphe...

~%

3-amino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-45-4

3-amino-1-(4-me...

1-(4-methoxyphenyl)-3-methyl-3-phenylsulfanylazetidin-2-one Structure

87568-30-7

1-(4-methoxyphe...

~%

3-amino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-45-4

3-amino-1-(4-me...

3-(benzenesulfinyl)-1-(4-methoxyphenyl)-3-methylazetidin-2-one Structure

87568-42-1

3-(benzenesulfi...

~%

3-amino-1-(4-methoxyphenyl)azetidin-2-one Structure

87568-45-4

3-amino-1-(4-me...

4-but-3-enylazetidin-2-one Structure

74373-13-0

4-but-3-enylaze...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

4-(4-chloro-3-phenylsulfanylbutyl)-1-phenylsulfanylazetidin-2-one Structure

87568-55-6

4-(4-chloro-3-p...

4-(3-chloro-4-phenylsulfanylbutyl)-1-phenylsulfanylazetidin-2-one Structure

87568-54-5

4-(3-chloro-4-p...

4-but-3-enylazetidin-2-one Structure

74373-13-0

4-but-3-enylaze...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

4-(4-chloro-3-phenylsulfanylbutyl)-1-phenylsulfanylazetidin-2-one Structure

87568-55-6

4-(4-chloro-3-p...

4-(3-chloro-4-phenylsulfanylbutyl)-1-phenylsulfanylazetidin-2-one Structure

87568-54-5

4-(3-chloro-4-p...

N/A Structure

17645-29-3

N/A

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~95%

3-chloro-2-methyl-N-phenyl-2-phenylsulfanylbutanamide Structure

83375-47-7

3-chloro-2-meth...

4-but-3-enylazetidin-2-one Structure

74373-13-0

4-but-3-enylaze...

~%

4-(3-chloro-4-phenylsulfanylbutyl)azetidin-2-one Structure

87568-56-7

4-(3-chloro-4-p...

4-but-3-enylazetidin-2-one Structure

74373-13-0

4-but-3-enylaze...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

4-(4-chloro-3-phenylsulfanylbutyl)azetidin-2-one Structure

74373-19-6

4-(4-chloro-3-p...

4-(3-chloro-4-phenylsulfanylbutyl)azetidin-2-one Structure

87568-56-7

4-(3-chloro-4-p...

4-but-3-enyl-1-[tert-butyl(dimethyl)silyl]azetidin-2-one Structure

109975-76-0

4-but-3-enyl-1-...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

4-(4-chloro-3-phenylsulfanylbutyl)azetidin-2-one Structure

74373-19-6

4-(4-chloro-3-p...

4-(3-chloro-4-phenylsulfanylbutyl)azetidin-2-one Structure

87568-56-7

4-(3-chloro-4-p...

3-(((benzyloxy)carbonyl)amino)-1-(p-methoxyphenyl)azetidin-2-one Structure

87568-46-5

3-(((benzyloxy)...

~59%

benzyl N-(2-oxoazetidin-3-yl)carbamate Structure

59511-72-7

benzyl N-(2-oxo...

3-(benzenesulfinyl)-1-(4-methoxyphenyl)-3-methylazetidin-2-one Structure

87568-42-1

3-(benzenesulfi...

~79%

1-(4-methoxyphenyl)-3-methylideneazetidin-2-one Structure

69193-56-2

1-(4-methoxyphe...

N-(4-METHOXY-PHENYL)-2-METHYL-ACRYLAMIDE Structure

7274-71-7

N-(4-METHOXY-PH...

~%

1-(4-methoxyphenyl)-3-methylideneazetidin-2-one Structure

69193-56-2

1-(4-methoxyphe...

1-(4-methoxyphenyl)-3-methyl-3-phenylsulfanylazetidin-2-one Structure

87568-30-7

1-(4-methoxyphe...

~%

1-(4-methoxyphenyl)-3-methylideneazetidin-2-one Structure

69193-56-2

1-(4-methoxyphe...

N-(4-METHOXY-PHENYL)-2-METHYL-ACRYLAMIDE Structure

7274-71-7

N-(4-METHOXY-PH...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

3-chloro-N-(4-methoxyphenyl)-2-methyl-2-phenylsulfanylpropanamide Structure

87568-26-1

3-chloro-N-(4-m...

2-chloro-N-(4-methoxyphenyl)-2-methyl-3-phenylsulfanylpropanamide Structure

87568-28-3

2-chloro-N-(4-m...

N-Phenylacrylamide Structure

2210-24-4

N-Phenylacrylamide

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

2,3-dichloro-N-phenyl-2-phenylsulfanylpropanamide Structure

83375-58-0

2,3-dichloro-N-...

2,3-dichloro-N-phenyl-2-phenylsulfanylpropanamide Structure

83375-58-0

2,3-dichloro-N-...

~35%

3-chloro-1-phenyl-3-phenylsulfanylazetidin-2-one Structure

83375-59-1

3-chloro-1-phen...

N-Phenylacrylamide Structure

2210-24-4

N-Phenylacrylamide

~%

3-chloro-1-phenyl-3-phenylsulfanylazetidin-2-one Structure

83375-59-1

3-chloro-1-phen...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

3-chloro-1-phenyl-3-phenylsulfanylazetidin-2-one Structure

83375-59-1

3-chloro-1-phen...

N-benzylmethacrylamide Structure

3219-55-4

N-benzylmethacr...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~22%

α-Phenylthio-β-chloroisobuttersaeurebenzylamid Structure

34880-23-4

α-Phenylthio-β-...

N-benzyl-2-chloro-2-methyl-3-phenylsulfanylpropanamide Structure

83375-60-4

N-benzyl-2-chlo...

N-(4-METHOXY-PHENYL)-2-METHYL-ACRYLAMIDE Structure

7274-71-7

N-(4-METHOXY-PH...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

3-chloro-N-(4-methoxyphenyl)-2-methyl-2-phenylsulfanylpropanamide Structure

87568-26-1

3-chloro-N-(4-m...

2-chloro-N-(4-methoxyphenyl)-2-methyl-3-phenylsulfanylpropanamide Structure

87568-28-3

2-chloro-N-(4-m...

α-Phenylthio-β-chloroisobuttersaeurebenzylamid Structure

34880-23-4

α-Phenylthio-β-...

~94%

1-benzyl-3-methyl-3-phenylsulfanylazetidin-2-one Structure

83375-61-5

1-benzyl-3-meth...

N-benzylmethacrylamide Structure

3219-55-4

N-benzylmethacr...

~%

1-benzyl-3-methyl-3-phenylsulfanylazetidin-2-one Structure

83375-61-5

1-benzyl-3-meth...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

1-benzyl-3-methyl-3-phenylsulfanylazetidin-2-one Structure

83375-61-5

1-benzyl-3-meth...

N-benzylmethacrylamide Structure

3219-55-4

N-benzylmethacr...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

1-benzyl-3-methyl-3-phenylsulfanylazetidin-2-one Structure

83375-61-5

1-benzyl-3-meth...

N-(4-METHOXY-PHENYL)-2-METHYL-ACRYLAMIDE Structure

7274-71-7

N-(4-METHOXY-PH...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

1-(4-methoxyphenyl)-3-methyl-3-phenylsulfanylazetidin-2-one Structure

87568-30-7

1-(4-methoxyphe...

1-(4-methoxyphenyl)-3-methyl-3-phenylsulfanylazetidin-2-one Structure

87568-30-7

1-(4-methoxyphe...

~98%

3-(benzenesulfinyl)-1-(4-methoxyphenyl)-3-methylazetidin-2-one Structure

87568-42-1

3-(benzenesulfi...

N-(4-METHOXY-PHENYL)-2-METHYL-ACRYLAMIDE Structure

7274-71-7

N-(4-METHOXY-PH...

~%

3-(benzenesulfinyl)-1-(4-methoxyphenyl)-3-methylazetidin-2-one Structure

87568-42-1

3-(benzenesulfi...

(Chlorosulfanyl)benzene Structure

931-59-9

(Chlorosulfanyl...

~%

3-(benzenesulfinyl)-1-(4-methoxyphenyl)-3-methylazetidin-2-one Structure

87568-42-1

3-(benzenesulfi...


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