HCID 68558105, compound → HCID 16093681, compound

HRID 2381921Notes

Reaction equation

HRID 2381921 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:7][CH:8]([OH:11])CO)[CH3:2]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:7][CH:8]=[O:11])[CH3:2]

Participants

3

Reactant 1

HCID 68558105HCID 68558105, compound

Product 1

HCID 16093681HCID 16093681, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [benzyloxycarbonyl-(2,3-dihydroxy-propyl)-amino]-acetic acid ethyl ester (1.98 g, 6.37 mmol) in DCM (30 mL) is added NaIO4-impregnated silica (13.04 g). The slurry is stirred rapidly for 4.5 h, and then filtered through a coarse porosity sintered glass funnel. The filtrate is concentrated to afford [benzyloxycarbonyl-(2-oxo-ethyl)-amino]-acetic acid ethyl ester (1.65 g, 92%). MS: 280 (M+H); 1H NMR (300 MHz, CDCl3) δ 9.60-9.68 (m, 1H), 7.26-7.40 (m, 5H), 510-5.19 (m, 2H), 4.00-4.22 (m, 6H), 1.18-1.30 (m, 3H). (see Y.-L. Zhong, T. K. M. Shing J. Org. Chem. 1997, 62 (8), 2622-2624).

Workup

  1. filtrationfiltered through a coarse porosity sintered glass funnel
  2. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-71b7d3a4d5294170b401a28e1e4f8450
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

Loading…