(2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)-4-mercaptopyrrolidine → (3S,4S)-4-[(1R)-1-{((2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)pyrrolidin-4-ylthio)thiocarbonyl}ethyl]-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-2-oxoazetidine

HRID 1464733Notes

Reaction equation

HRID 1464733 reaction equation
[C:1]([Si:5]([CH3:26])([CH3:25])[O:6][C@@H:7]([C@@H:9]1[C@@H:12]([C@H:13]([C:15](SC2C=CC=CC=2)=[S:16])[CH3:14])[NH:11][C:10]1=[O:24])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:27]([O:30][C:31]([N:33]1[CH2:37][C@@H:36]([SH:38])[CH2:35][C@H:34]1[C:39](=[O:43])[N:40]([CH3:42])[CH3:41])=[O:32])[CH:28]=[CH2:29]>C(#N)C>[CH2:27]([O:30][C:31]([N:33]1[CH2:37][C@@H:36]([S:38][C:15]([C@@H:13]([C@H:12]2[NH:11][C:10](=[O:24])[C@@H:9]2[C@H:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:25])[CH3:26])[CH3:8])[CH3:14])=[S:16])[CH2:35][C@H:34]1[C:39](=[O:43])[N:40]([CH3:41])[CH3:42])=[O:32])[CH:28]=[CH2:29]

Participants

4

Reactant 2

HCID 10083864(2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)-4-mercaptopyrrolidineHCID 22851409(3S,4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(phenylthio)thiocarbonyl}ethyl]-2-oxoazetidine

Product 1

HCID 22851410(3S,4S)-4-[(1R)-1-{((2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)pyrrolidin-4-ylthio)thiocarbonyl}ethyl]-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-2-oxoazetidineYield 77.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of (3S,4S)-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(phenylthio)thiocarbonyl}ethyl]-2-oxoazetidine (100 mg) and cuprous chloride (30 mg) in acetonitrile (1 ml) was added (2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)-4-mercaptopyrrolidine (130 mg) and the mixture was stirred at the ambient temperature for 5 hours. The mixture was purified by preparative thin layer chromatography (developed with ethyl acetate) to give (3S,4S)-4-[(1R)-1-{((2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)pyrrolidin- 4-ylthio)thiocarbonyl}ethyl]-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-2-oxoazetidine (105 mg).

Workup

  1. customThe mixture was purified by preparative thin layer chromatography (developed with ethyl acetate)

Sources & evidence

ORD record
ord-43e83161d441404fac44f5e2dc50e56e
Source dataset
uspto-grants-1994_04
Patent number
US05306816

Reaction notes

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