4-Methylanthranilic acid → 3-[5-(1-t-Butoxyformamido)valeramido]-p-toluic acid

HRID 2248510Notes

Reaction equation

HRID 2248510 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][C:17]1[CH:18]=[C:19]([CH3:26])[CH:20]=[CH:21][C:22]=1[C:23]([OH:25])=[O:24]>>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:16][C:17]1[CH:18]=[C:19]([CH3:26])[CH:20]=[CH:21][C:22]=1[C:23]([OH:25])=[O:24])=[O:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 753164-Methylanthranilic acidHCID 5458485-(((Tert-butoxy)carbonyl)amino)pentanoic acid

Product 1

HCID 570766503-[5-(1-t-Butoxyformamido)valeramido]-p-toluic acid

Procedure

For the preparation of the starting material, 5-[1-(t-butoxy)formamido]valeric acid and 3-amino-p-toluic acid are coupled to give 3-[5-(1-t-butoxyformamido)valeramido]-p-toluic acid, m.p. 212° C., and the latter is coupled with β-alanine benzyl ester to give N-[3-[5-(1-t-butoxyformamido)valeramido]-p-toluoyl]-β-alanine benzyl ester, m.p. 112°-113° C.

Sources & evidence

ORD record
ord-9fccd688e62741b1b3aa8afa5bb992ad
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

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