2-Tert-butoxycarbonylamino-4-hydroxy-butyric acid benzyl ester → 2-Tert-butoxycarbonylamino-4-oxo-butyric acid benzyl ester

HRID 507429Notes

Reaction equation

HRID 507429 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[CH:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:22])[CH:10]([NH:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:11][CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 113473932-Tert-butoxycarbonylamino-4-hydroxy-butyric acid benzyl esterHCID 178418287HCID 178418287, compound

Product 1

HCID 143577952-Tert-butoxycarbonylamino-4-oxo-butyric acid benzyl esterYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 (1.65 g, 5.50 mmol) in CH2Cl2 (4 mL) was added 4 Å molecular sieves (4.5 g) and PCC (2.36 g, 11 mmol). Then the mixture was stirred for 2 hours, filtered through silica gel column until the filtrate was nearly colorless. The filtrate was evaporated to dryness and the crude product (1.4 g, 82%) was obtained and was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ1.43 (s, 9 H), 2.97-3.16 (m, 2 H), 4.63 (s, 1H), 5.17 (s, 2 H), 5.40 (d, 1 H), 7.33 (m, 5 H), 9.71 (s, 1 H).

Workup

  1. filtrationfiltered through silica gel column until the filtrate
  2. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-107f793e4c2942b6877745d90e9fc2e0
Source dataset
uspto-grants-2010_08
Patent number
US07786163B2

Reaction notes

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