反应 #742290

ord-922cb2edb72b4d0c9d9b8d6913ed98cd

反应方程式

O
water
C[C@@H](CO)NC(=O)OC(C)(C)C
tert-butyl[(1S)-2-hydroxy-1-methylethyl]carbamate
CC(C)(C)C(=O)Cl
pivaloyl chloride
CCN(CC)CC
Et3N
C[C@@H](COC(=O)C(C)(C)C)NC(=O)OC(C)(C)C
(2S)-2-[(tert-butoxycarbonyl)-amino]-propyl pivalate

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他the organic phase was separated
  2. 2
    洗涤washed with 10% aqueous citric acid
  3. 3
    其他The residue was purified by column chromatography on silica gel eluting with 92:8 PE/EtOAc

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08071568B2uspto-grants-2011_12