2-{[(Benzyloxy)carbonyl]amino}-3-(4-cyanophenyl)propanoic acid → N-[N-[N-(benzyloxycarbonyl)-3-(p-cyanophenyl)-DL-alanyl]glycyl]-beta-alanine benzyl ester
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:22]([OH:24])=O)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[CH2:32]([O:39][C:40](=[O:48])[CH2:41][CH2:42][NH:43][C:44](=[O:47])[CH2:45][NH2:46])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:32]([O:39][C:40](=[O:48])[CH2:41][CH2:42][NH:43][C:44](=[O:47])[CH2:45][NH:46][C:22](=[O:24])[CH:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1Participants
Procedure
For the preparation of the ester starting material, N-(benzyloxycarbonyl)-3-(p-cyanophenyl)-DL-alanine and N-glycyl-β-alanine benzyl ester trifluoroacetate are coupled to give N-[N-[N-(benzyloxycarbonyl)-3-(p-cyanophenyl)-DL-alanyl]glycyl]-β-alanine benzyl ester, m.p. 134°-135° C. Therefrom with hydrogen sulphide and triethylamine in pyridine there is obtained N-[N-[N-(benzyloxycarbonyl)-3-[p-(thiocarbamoyl)phenyl]-DL-alanyl]glycyl]-β-alanine benzyl ester m.p.150°-151° C. Reaction with methyl iodide in acetone, subsequent reaction with ammonium acetate in methanol and treatment with benzyl chloroformate and triethylamine in THF give N-[N-[N-(benzyloxycarbonyl)-3-[p-[N-(benzyloxycarbonyl)-amidino]phenyl]-DL-alanyl]glycyl]-β-alanine benzyl ester, MS: 694 (100, M+H).
Sources & evidence
- ORD record
- ord-4fd21a1cc51b4d8282d754e4ae64469c
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05663297
Reaction notes
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