Dichloromethane → (3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine

HRID 1464726Notes

Reaction equation

HRID 1464726 reaction equation
ClCCl.[C:4]([Si:8]([CH3:24])([CH3:23])[O:9][C@@H:10]([C@@H:12]1[C@@H:15]([C@H:16]([C:18]([S:20][CH3:21])=[S:19])[CH3:17])[NH:14][C:13]1=[O:22])[CH3:11])([CH3:7])([CH3:6])[CH3:5].[Si](O[C@@H]([C@@H]1[C@@H]([C@@H](C(SC)=S)C)NC1=O)C)(C(C)(C)C)(C)C.Cl[C:47](=[O:54])[C:48]([O:50][CH2:51][CH:52]=[CH2:53])=[O:49]>C(N(CC)CC)C>[CH2:51]([O:50][C:48](=[O:49])[C:47]([N:14]1[C@H:15]([C@H:16]([C:18]([S:20][CH3:21])=[S:19])[CH3:17])[C@@H:12]([C@H:10]([O:9][Si:8]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:23])[CH3:24])[CH3:11])[C:13]1=[O:22])=[O:54])[CH:52]=[CH2:53]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 3018516Allyl chlorooxoacetateHCID 57193536(3S,4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1S)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidineHCID 57309161(3S,4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-[(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine

Product 1

HCID 86747781(3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidineYield 52.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of dichloromethane (32.6 mg) and a mixture (33.1 mg) of (3S,4S)-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine and (3S,4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1S)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine were added triethylamine (30.4 mg) and allyl chloroglyoxylate (32.6 mg) successively at 0° C. After stirring for 10 minutes at the same temperature, the solution was washed with water, 1N hydrochloric acid, brine, and dried. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (5% diethyl ether-hexane) to afford a mixture (23 mg) of (3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine and (3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[1S)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine.

Workup

  1. washthe solution was washed with water, 1N hydrochloric acid, brine
  2. customdried
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography (5% diethyl ether-hexane)

Sources & evidence

ORD record
ord-4f04df132e48462c8d5931f18fe46f72
Source dataset
uspto-grants-1994_04
Patent number
US05306816

Reaction notes

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