N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → 5-[3-(1-t-Butoxyformamido)propionamido]-2-nitrobenzoic acid

HRID 2248504Notes

Reaction equation

HRID 2248504 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[C:19]([CH:23]=1)[C:20]([OH:22])=[O:21]>>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([NH:14][C:15]1[CH:16]=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[C:19]([CH:23]=1)[C:20]([OH:22])=[O:21])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 832985-Amino-2-nitrobenzoic acid

Product 1

HCID 540309035-[3-(1-t-Butoxyformamido)propionamido]-2-nitrobenzoic acid

Procedure

For the preparation of the ester starting material, MS: 468 (18, M+NH4), 451 (100, M+H), N-(t-butoxycarbonyl)-β-alanine and 5-amino-2-nitrobenzoic acid are reacted to give 5-[3-(1-t-butoxyformamido)propionamido]-2-nitrobenzoic acid, MS: 354 (17, M+H), the latter is reacted with β-alanine t-butyl ester to give N-[5-[3-(1-t-butoxyformamido)propionamido]-2-nitrobenzoyl]-β-alanine t-butyl ester and this is hydrogenated on Pd/C in ethanol.

Sources & evidence

ORD record
ord-62876e678b444270a08635ad5f44150e
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

Loading…