(3S, 4R)3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-[1-methyl-2-p-nitrobenzyloxycarbonylaminoethylthio(thiocarbonyl)]thioazetidin-2-one → (3S, 4R)-3-[(R)-1-t-Butyldimethylsilyloxyethyl]-1-[1-hydroxy-1-(p-nitrobenzyloxycarbonyl)methyl]-4-[1-methyl-2-p-nitrobenzyloxycarbonylaminoethylthio(thiocarbonyl)]thioazetidin-2-one

Participants

Reaction Steps

A mixture of 230 mg (0.40 mmole) of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-[1-methyl-2-p-nitrobenzyloxycarbonylaminoethylthio(thiocarbonyl)]thioazetidin-2-one, 182 mg (0.80 mmole) of p-nitrobenzyl glyoxylate hydrate and 5 ml of benzene was heated under reflux for 10 hours. After completion of the reaction the solvent was distilled off and the resulting residue was subjected to column chromatography through 10 g of silica gel eluted with a 7-10% v/v solution of ethyl acetate in benzene to afford 234 mg (yield 75%) of the desired product as a yellow oil.

Provenance & Evidence