Caffeic Acid → (2S)-N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-N'-trityl-butanediamide
반응식
C1C2C(COC([NH:18][C@H:19]([C:43]([NH:45][CH2:46][CH2:47][C:48]3[CH:55]=[CH:54][C:52]([OH:53])=[C:50]([OH:51])[CH:49]=3)=[O:44])[CH2:20][C:21](=[O:42])[NH:22][C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.[C:56]([OH:68])(=O)/[CH:57]=[CH:58]/[C:59]1[CH:66]=[CH:65][C:63]([OH:64])=[C:61]([OH:62])[CH:60]=1>>[C:56]([NH:18][C@H:19]([C:43]([NH:45][CH2:46][CH2:47][C:48]1[CH:55]=[CH:54][C:52]([OH:53])=[C:50]([OH:51])[CH:49]=1)=[O:44])[CH2:20][C:21](=[O:42])[NH:22][C:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:68])/[CH:57]=[CH:58]/[C:59]1[CH:66]=[CH:65][C:63]([OH:64])=[C:61]([OH:62])[CH:60]=1참가 물질
3
실험 절차
N-[Nα-(9-fluorenylmethoxycarbonyl)-Nγ-trityl-L-asparagyl]dopamine (1.0 g, 1.5 mmol) was deprotected according to the indications of general procedure G. The intermediate was coupled with caffeic acid (348 mg, 2.2 mmol) following general procedure D. The crude material was purified by flash chromatography using a solvent gradient from 30% to 70% EtOAc/CHCl3 containing 1% AcOH. The final product was obtained as yellow powder (400 mg, 44%).