Reaktion #742290

ord-922cb2edb72b4d0c9d9b8d6913ed98cd

Reaktionsgleichung

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

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08071568B2uspto-grants-2011_12