HCID 86605286, compound → HCID 77222088, compound

HRID 1348606Notes

Reaction equation

HRID 1348606 reaction equation
[CH2:1]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:9]([CH:13]([O:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[N+:26]([O-])=O)[C:14]([F:17])([F:16])[F:15])[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Ni]>[NH2:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[O:18][CH:13]([C:14]([F:15])([F:16])[F:17])[CH:9]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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 86605286HCID 86605286, compound

Product 1

HCID 77222088HCID 77222088, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

5.00 g (10.2 mmol) (2S,3S and 2R,3R)-2-dibenzylamino-4,4,4-trifluoro-3-(4-fluoro-2-nitro-phenoxy)-butyric acid acid in 300 ml methanol were hydrogenated with 1.19 g Raney-Nickel. Filtration and removal of the solvent by distillation yielded 4.19 g (89%) racemic (2S,3S and 2R,3R)-3-(2-amino-4-fluoro-phenoxy)-2-dibenzylamino-4,4,4-trifluoro-butyric acid as light yellow oil, MS m/e (%): 461.2 (M−H+, 100).

Workup

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

Sources & evidence

ORD record
ord-569f003d742b4fc2aefe884d98a6c459
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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