Acetic Anhydride → N-acetyl-S-phenyl-cysteine methyl ester

Participants

Reaction Steps

1.00 gram (4.22 mmoles) of the 2-azido-3-phenylmercapto-propionic acid methyl ester obtained in Example 2 was dissolved in 5 ml of acetic anhydride and then was added 1 mole % of rhenium VII sulfide based on the azido compound employed. Under vigorous stirring there was led hydrogen through the solution for 24 hours at 70° C. After the end of the reaction the solvent was drawn off under reduced pressure on the rotary evaporator, the product taken up in diethyl ether and the catalyst filtered off. Chromatography on a silica gel column with petroleum ether/ethyl acetate (volume ratio 1:1) gave 0.50 gram (47% of theory) of N-acetyl-S-phenyl-cysteine methyl ester as a colorless oil.

Provenance & Evidence