Sodium Hydroxide → (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-dihydroxypropylthio)propanoate

Participants

Reaction Steps

A solution of (2S)-(+)-glycidyl-4-nitrobenzoate (1.1 eq) and 1M NaOH (1.1 eq) in tBuOH (0.1 M) was stirred at room temperature until complete hydrolysis of the nitrobenzoate was observed (30 minutes). To the resulting mixture, a solution of (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-mercaptopropanoate (12, 1 eq) in tBuOH (1 M) was introduced and the reaction stirred at room temperature for 15 hours. The reaction mixture was concentrated en vaccuo to remove tBuOH then dissolved in EtOAc. The EtOAc solution was washed three times with water, once with brine, then dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient of 0-90% EtOAc/Hex to give the title product as a colorless viscous oil.

Provenance & Evidence