Reaction #742290

Reaction equation

water

tert-butyl[(1S)-2-hydroxy-1-methylethyl]carbamate

pivaloyl chloride

Et3N

→

(2S)-2-[(tert-butoxycarbonyl)-amino]-propyl pivalate

Solvents

DCM

Conditions

Workup

1. 1
   Otherthe organic phase was separated
2. 2
   Washwashed with 10% aqueous citric acid
3. 3
   OtherThe residue was purified by column chromatography on silica gel eluting with 92:8 PE/EtOAc

Procedure

To a solution of the commercially available tert-butyl[(1S)-2-hydroxy-1-methylethyl]carbamate (1.0 eq.) in DCM (0.19M), pivaloyl chloride (1.1 eq.) and Et3N (1.1 eq.) were added. The reaction mixture was stirred at RT for 48 h, then water was added and the organic phase was separated and washed with 10% aqueous citric acid. The residue was purified by column chromatography on silica gel eluting with 92:8 PE/EtOAc.

Source