HCID 67077116, compound → HCID 67077443, compound

HRID 1348673Notes

Reaction equation

HRID 1348673 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([O:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[N+:39]([O-])=O)[CH:12]([N:16]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Ni]>[NH2:39][C:33]1[CH:34]=[C:35]([F:38])[CH:36]=[CH:37][C:32]=1[O:31][CH:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:12]([N:16]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:13]([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 67077116HCID 67077116, compound

Product 1

HCID 67077443HCID 67077443, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

6.00 g (11 mmol) racemic (2R,3R and 2S,3S)-5-Benzyloxy-2-dibenzylamino-3-(4-fluoro-2-nitro-phenoxy)-pentanoic acid in 100 ml methanol were hydrogenated with 1.5 g Raney-Nickel. Filtration and removal of the solvent by distillation yielded 5.57 g (98%) (2R,3R and 2S,3S)-3-(2-amino-4-fluoro-phenoxy)-5-benzyloxy-2-dibenzylamino-pentanoic acid as foam, MS m/e (%): 529.5 (M+H+, 100).

Workup

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

Sources & evidence

ORD record
ord-c2613c6d36ed4bd8a6b968019d644e89
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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