N-[(1,1-Dimethylethoxy)carbonyl]-3-[(2-nitrophenyl)amino]-L-alanine → (2S)-3-[(2-aminophenyl)amino]-2-{[(tert-butoxy)carbonyl]amino}propanoic acid

HRID 1481891Notes

Reaction equation

HRID 1481891 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][CH2:13][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 22881947N-[(1,1-Dimethylethoxy)carbonyl]-3-[(2-nitrophenyl)amino]-L-alanine

Product 1

HCID 22881946(2S)-3-[(2-aminophenyl)amino]-2-{[(tert-butoxy)carbonyl]amino}propanoic acidYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (S)-2-tert-butoxycarbonylamino-3-(2-nitro-phenylamino)-propionic acid (Aldrich) (10 g, 30.76 mmol) in MeOH (100 mL) was purged with argon for 30 min, and 10% Pd—C (1 g) was added to the solution. The resulting mixture was hydrogenated using a balloon for 18 h at RT. The mixture was filtered through Celite and the filtrate was concentrated and the resulting material was triturated with hexane to afford (S)-3-(2-amino-phenylamino)-2-tert-butoxycarbonylamino-propionic acid (8.5 g, 93%) as brown solid. LC-MS: 296 (M+H).

Workup

  1. customfor 18 h
  2. customat RT
  3. filtrationThe mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated
  5. customthe resulting material was triturated with hexane

Sources & evidence

ORD record
ord-12f062272b4c4316a0109667c77a6203
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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