3,4-Di-(4-fluorobenzyloxy)caffeic acid → n-[Nalpha-(3,4-di-(4-fluorobenzyloxy)caffeoyl)-ndelta-trityl-l-glutaminyl]-3-hydroxy-4-methoxyaniline
Reaction equation
C1C2C(COC([NH:18][C@H:19]([C:44]([NH:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([OH:55])[CH:48]=3)=[O:45])[CH2:20][CH2:21][C:22](=[O:43])[NH:23][C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.[F:56][C:57]1[CH:86]=[CH:85][C:60]([CH2:61][O:62][C:63]2([OH:84])[C:73](OCC3C=CC(F)=CC=3)([OH:74])[CH:72]=[CH:71][C:65](/[CH:66]=[CH:67]/[C:68]([OH:70])=[O:69])=[CH:64]2)=[CH:59][CH:58]=1>>[F:56][C:57]1[CH:86]=[CH:85][C:60]([CH2:61][O:62][C:63]2([OH:84])[C:68]([O:69][CH2:61][C:60]3[CH:85]=[CH:86][C:57]([F:56])=[CH:58][CH:59]=3)([OH:70])[CH:67]=[CH:66][C:65](/[CH:71]=[CH:72]/[C:73]([NH:18][C@H:19]([C:44]([NH:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([OH:55])[CH:48]=3)=[O:45])[CH2:20][CH2:21][C:22](=[O:43])[NH:23][C:24]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:74])=[CH:64]2)=[CH:59][CH:58]=1Participants
3
Procedure
The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nδ-trityl-L-glutaminyl]-3-hydroxy-4-methoxyaniline (565 mg, 0.8 mmol, example 109, step A) as described for example 109 (step B) using 3,4-di-(4-fluorobenzyloxy)caffeic acid (459 mg, 1.2 mmol) instead of N-(4-fluorobenzyl)indole-2-carboxylic acid. The crude material was purified by flash chromatography using successively 15%, 20% and 30% EtOAc/CH2Cl2 as the eluent. The title compound was obtained as white crystals (250 mg, 37%).
Workup
- customThe crude material was purified by flash chromatography
Sources & evidence
- ORD record
- ord-490f4ae4a4494ba2ae5776ab4e14353b
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06528655B1
Reaction notes
Loading…