5-Amino-2-chlorobenzoic acid → HCID 54278292, compound

HRID 2248497Notes

Reaction equation

HRID 2248497 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]=[CH:20][C:21]([Cl:27])=[C:22]([CH:26]=1)[C:23]([OH:25])=[O:24]>>[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]=[CH:20][C:21]([Cl:27])=[C:22]([CH:26]=1)[C:23]([OH:25])=[O:24])=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 378795-Amino-2-chlorobenzoic acidHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acid

Product 1

HCID 54278292HCID 54278292, compound

Procedure

For the preparation of the starting material [MS: 456 (1, M+H)], 6-(1-t-butyoxyformamido)hexanoic acid and 5-amino-2-chlorobenzoic acid are coupled to give 5-[6-(1-t-butoxyformamido)hexanamido]-2-chlorobenzoic acid, MS: 385 (2, M+H), the latter is coupled with β-alanine methyl ester to give N-[5-[6-(1-t-butoxyformamido)hexanamido]-2-chlorobenzoyl-β-alanine methyl ester, MS: 470 (14, M+H), and this is then saponified in methanolic sodium hydroxide solution.

Sources & evidence

ORD record
ord-9bfe3eeb2a684e5d98fb5cbda123d300
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

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