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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2230460Generated: October 31, 2026

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

https://huagongshe.com/reaction/2230460

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN-[(1,1-Dimethylethoxy)carbonyl]-3-[(2-nitrophenyl)amino]-L-alanineHCID 22881947—
CatalystPalladiumHCID 23938—
SolventMethanolHCID 887—
Product(2S)-3-[(2-aminophenyl)amino]-2-{[(tert-butoxy)carbonyl]amino}propanoic acidHCID 2288194699.9%

Reaction Steps

At 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) δ6.75-6.70 (3H,m), 6.65-6.58 (1H, m), 4.35-4.3 1H, m), 3.6-3.38 (2H, m), 1.45 (9H, s).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06423840B1
Source datasetuspto-grants-2002_07
ORD IDord-f1de37e61d904c95a36eb4cfbad53ba6
Source noteuspto-grants-2002_07