3-Amino-5-nitrobenzoic acid → 3-[6-(1-t-Butoxyformamido)hexanamido]-5-nitrobenzoic acid

HRID 2248496Notes

Reaction equation

HRID 2248496 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)[C:21]([OH:23])=[O:22]>>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)[C:21]([OH:23])=[O:22])=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 2393423-Amino-5-nitrobenzoic acidHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acid

Product 1

HCID 543331993-[6-(1-t-Butoxyformamido)hexanamido]-5-nitrobenzoic acid

Procedure

For the preparation of the starting material, MS: 367 (M-BOC+H), 6-(1-t-butoxyformamido)hexanoic acid and 3-amino-5-nitrobenzoic acid are reacted to give 3-[6-(1-t-butoxyformamido)hexanamido]-5-nitrobenzoic acid, MS: 396 (2, M+H), and the latter is reacted with β-alanine methyl ester to give N-[3-[6-(1-t-butoxyformamido)hexanamido]-5-nitrobenzoyl]-β-alanine methyl ester, MS: 381 (100, M-Boc+H). This is then saponified in methanolic sodium hydroxide solution.

Workup

  1. customFor the preparation of the starting material, MS

Sources & evidence

ORD record
ord-29908c88e5f44a6a911e9fcc30c29146
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

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