3-Cyanobenzoic acid → N-[m-(m-cyanobenzamido)benzoyl]-beta-alanine benzyl ester

HRID 2248511Notes

Reaction equation

HRID 2248511 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)#[N:2].FC(F)(F)C(O)=O.[CH2:19]([O:26][C:27](=[O:40])[CH2:28][CH2:29][NH:30][C:31](=[O:39])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([NH2:38])[CH:33]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([O:26][C:27](=[O:40])[CH2:28][CH2:29][NH:30][C:31](=[O:39])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([NH:38][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:33]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 158753-Cyanobenzoic acidHCID 67827899N-(m-aminobenzoyl)-beta-alanine benzyl ester trifluoroacetate

Product 1

HCID 19996479N-[m-(m-cyanobenzamido)benzoyl]-beta-alanine benzyl ester

Procedure

For the preparation of the starting material, m.p. 182°-183° C., 3-cyanobenzoic acid and N-(m-aminobenzoyl)-β-alanine benzyl ester trifluoroacetate are coupled to give N-[m-(m-cyanobenzamido)benzoyl]-β-alanine benzyl ester, MS: 428 (100, M+H), and this is converted with hydrogen sulphide and triethylamine in pyridine into N-[m-[m-(thiocarbamoyl)benzamido]benzoyl]-β-alanine benzyl ester, m.p. 128°-131° C. The latter is then reacted with methyl iodide in acetone and subsequently with ammonium acetate in methanol and treated with benzyl chloroformate and triethylamine in THF.

Sources & evidence

ORD record
ord-6122a6974c19437da69fed91fba118f8
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

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