(S)-2-tert-Butoxycarbonylamino-3-(2-chloro-6-nitro-phenoxy)-propionic acid benzyl ester → (S)-3-(2-Amino-6-chloro-phenoxy)-2-tert-butoxycarbonylamino-propionic acid

HRID 1348590Notes

Reaction equation

HRID 1348590 reaction equation
C([O:8][C:9](=[O:31])[C@@H:10]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:11][O:12][C:13]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:22])C1C=CC=CC=1>[Ni]>[NH2:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:22])[C:13]=1[O:12][CH2:11][C@H:10]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[C:9]([OH:31])=[O:8]

Participants

3

Reactant 1

HCID 67076911(S)-2-tert-Butoxycarbonylamino-3-(2-chloro-6-nitro-phenoxy)-propionic acid benzyl ester

Product 1

HCID 67076750(S)-3-(2-Amino-6-chloro-phenoxy)-2-tert-butoxycarbonylamino-propionic acidYield 91%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

In an analogous manner to that described in example 5b), the hydrogenation of (S)-2-tert-butoxycarbonylamino-3-(2-chloro-6-nitro-phenoxy)-propionic acid benzyl ester using Raney-nickel instead of palladium as the catalyst yielded (91%) the title compound as a light brown foam, MS m/e (%): 329.3 (M−H+, 100).

Sources & evidence

ORD record
ord-7893781270ce4f2da780c98000c8d4ef
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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