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

HRID 1348641Notes

Reaction equation

HRID 1348641 reaction equation
[CH2:1]([N:8]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:9]([C:13]([O:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[N+:24]([O-])=O)([CH3:15])[CH3:14])[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Ni]>[NH2:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[O:16][C:13]([CH3:14])([CH3:15])[CH:9]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 210914022-Dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-3-methyl-butyric acid

Product 1

HCID 210914203-(2-Amino-4-fluoro-phenoxy)-2-dibenzylamino-3-methyl-butyric acidYield 96.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

0.10 g (0.22 mmol) 2-dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-3-methyl-butyric acid in 3.4 ml methanol were hydrogenated with 0.03 g Raney-Nickel. Filtration and removal of the solvent by distillation yielded 0.09 g (93%) 3-(2-amino-4-fluoro-phenoxy)-2-dibenzylamino-3-methyl-butyric acid as colorless solid, MS m/e (%): 423.3 (M+H+, 100).

Workup

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

Sources & evidence

ORD record
ord-2c671c2e387442ef945d9b7f9e16ebf5
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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