2-{[(Benzyloxy)carbonyl]amino}-3-(4-cyanophenyl)propanoic acid → N-[m-[[N-(benzyloxycarbonyl)-3-(p-cyanophenyl)-DL-alanyl]amino]benzoyl]-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:53])[CH2:41][CH2:42][NH:43][C:44](=[O:52])[C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([NH2:51])[CH:46]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:32]([O:39][C:40](=[O:53])[CH2:41][CH2:42][NH:43][C:44](=[O:52])[C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([NH:51][C:22](=[O:24])[CH:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=2)[NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH:46]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1Participants
3
Procedure
For the preparation of the ester starting material, MS: 756 (15, M+H), N-(benzyloxycarbonyl)-3-(p-cyanophenyl)-DL-alanine and N-(m-aminobenzoyl)-β-alanine benzyl ester trifluoroacetate are coupled to give N-[m-[[N-(benzyloxycarbonyl)-3-(p-cyanophenyl)-DL-alanyl]amino]benzoyl]-β-alanine benzyl ester, MS: 605 (15, M+H), and this is converted with hydrogen sulphide and triethylamine in pyridine into N-[m-[[N-(benzyloxycarbonyl)-3-[p-(thiocarbamoyl)phenyl]-DL-alanyl]amino]benzoyl]-β-alanine benzyl ester, m.p. 145°-146° C. (from ethyl acetate). 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-24dfc3d7000943f494e8424028215b60
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05039805
Reaction notes
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