HCID 67077050, compound → HCID 67077039, compound

HRID 1348631Notes

Reaction equation

HRID 1348631 reaction equation
[CH:1]1([CH:4]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[N+:32]([O-])=O)[CH:5]([N:9]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1>CO.[Ni]>[NH2:32][C:26]1[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=1[O:24][CH:4]([CH:1]1[CH2:3][CH2:2]1)[CH:5]([N:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 67077050HCID 67077050, compound

Product 1

HCID 67077039HCID 67077039, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1.47 g (3.17 mmol) racemic (2R,3S and 2S,3R)-3-Cyclopropyl-2-dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-propionic acid in 50 ml methanol were hydrogenated with 0.37 g Raney-Nickel. Filtration and removal of the solvent by distillation yielded 1.22 g (89%) racemic (2R,3S and 2S,3R)-3-(2-amino-4-fluoro-phenoxy)-3-cyclopropyl-2-dibenzylamino-propionic acid as light grey foam, MS m/e (%): 435.1 (M+H+, 100).

Workup

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

Sources & evidence

ORD record
ord-90dc856d3b0c4c3291fc93f103bd9445
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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