تفاعل #742290

ord-922cb2edb72b4d0c9d9b8d6913ed98cd

معادلة التفاعل

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

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08071568B2uspto-grants-2011_12