Water → HCID 22858518, compound

Participants

Reaction Conditions

Reaction Steps

206 g of methyl N-benzyloxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenylbutyrate was dissolved in 1,000 ml of methylene chloride and cooled to -10° C. After adding 79 g of triethylamine, 82.5 g of methanesulfonyl chloride was slowly added thereto under cooling at the same temperature. The obtained mixture was stirred at 15° to 0° C. for 1 hour and then 500 ml of water was added thereto to effect liquid/liquid separation. The organic layer was separated and washed successively with 1N hydrochloric acid, a 5% aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and concentrated under reduced pressure. Thus 253 g of methyl N-benzyloxycarbonyl-3(S)-amino-2(R)-methanesulfonyloxy-4-phenylbutyrate was obtained as a pale yellow, oily substance.

Provenance & Evidence