2-Benzyloxycarbonylamino-3-(2,6-difluorophenyl)acrylic acid methyl ester → HCID 67391680, compound

HRID 907596

Reaction equation

HRID 907596 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[CH:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[F:13]>C(O)C>[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[CH2:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[F:13]

Participants

3

Reactant 1

HCID 673920002-Benzyloxycarbonylamino-3-(2,6-difluorophenyl)acrylic acid methyl ester

Product 1

HCID 67391680HCID 67391680, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-benzyloxycarbonylamino-3-(2,6-difluorophenyl)acrylic acid methyl ester (14.4 mmol), and catalyst, (+)-1,2-bis-[(2S,5S)2,5-diethylphopholano]benzene (cyclooctadiene)rhodium (1) trifluoromethanesulfonate (Strem. Chemical No. 45-0151; 104 mg, 0.14 mmol) was dissolved in ethanol (150 ml). Hydrogenation was performed at 50 psi H2 at room temperature over 2 days. The solvent was then removed by rotary evaporation to give 2(S)-benzyloxycarbonylamino-3-(2,6-difluorophenyl)propionic acid methyl ester.

Workup

  1. customThe solvent was then removed by rotary evaporation

Sources & evidence

ORD record
ord-8762bbeee6134cd997ab4ab1dc2400e0
Source dataset
uspto-grants-2011_09
Patent number
US08013186B2

Linked notes

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