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

HRID 1464726

반응식

HRID 1464726 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4f04df132e48462c8d5931f18fe46f72
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306816

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