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

참여 물질

반응 단계

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.

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