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

HRID 1384715Notes

Reaction equation

HRID 1384715 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]>[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[NH2:21])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

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 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2S)-2-tert-Butoxycarbonylamino-3-(2-nitrophenylamino)propionic acid (12.65 g, 40.5 mmol) and 0.5 g of 10% Pd/C in 100 ml of MeOH under hydrogen at 1 atmosphere was stirred for 4 h. The solution was filtered through Celite 545 and the filtrate evaporated in vacuo to afford the 11.95 g of the title compound in quantitative yield as a dark brown solid that was used without purification: 1H NMR (CD3OD) δ 6.75-6.70 (3H,m), 6.65-6.58 (1H, m), 4.35-4.3 (1H, m), 3.6-3.38 (2H, m), 1.45 (9H, s).

Workup

  1. filtrationThe solution was filtered through Celite 545
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-22b6ae33478347018c41b865442c8221
Source dataset
uspto-grants-2001_07
Patent number
US06258948B1

Reaction notes

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