Caffeic Acid → (2S)-N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-N'-trityl-butanediamide
反応式
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]=1参加物
3
実験手順
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%).