2-Dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-4-phenyl-butyric acid → 3-(2-Amino-4-fluoro-phenoxy)-2-dibenzylamino-4-phenyl-butyric acid

HRID 1348620Notes

Reaction equation

HRID 1348620 reaction equation
[CH2:1]([N:8]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:9]([CH:13]([O:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[N+:29]([O-])=O)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Ni]>[NH2:29][C:23]1[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:22]=1[O:21][CH:13]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:9]([N:8]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 670768382-Dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-4-phenyl-butyric acid

Product 1

HCID 670767993-(2-Amino-4-fluoro-phenoxy)-2-dibenzylamino-4-phenyl-butyric acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

2.95 g (5.73 mmol) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-4-phenyl-butyric acid in 59 ml methanol were hydrogenated with 1.76 g Raney-Nickel. Filtration and removal of the solvent by distillation yielded 2.26 g (81%) racemic (2S,3R and 2R,3S)-3-(2-amino-4-fluoro-phenoxy)-2-dibenzylamino-4-phenyl-butyric acid as light yellow oil, MS m/e (%): 485.5 (M+H+, 100).

Workup

  1. filtrationFiltration and removal of the solvent
  2. distillationby distillation

Sources & evidence

ORD record
ord-89387782ee154d4ba08c6eb5b5a707b2
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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