5-Fluoroindole-2-carboxylic acid → (2S)-2-[(5-fluoro-1H-indole-2-carbonyl)amino]-N-(3-hydroxy-4-methoxy-phenyl)-N'-trityl-pentanediamide
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:58]=[C:59]2[C:63](=[CH:64][CH:65]=1)[NH:62][C:61]([C:66]([OH:68])=O)=[CH:60]2>>[F:56][C:57]1[CH:58]=[C:59]2[C:63](=[CH:64][CH:65]=1)[NH:62][C:61]([C:66]([NH:18][C@H:19]([C:44]([NH:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([OH:55])[CH:48]=1)=[O:45])[CH2:20][CH2:21][C:22](=[O:43])[NH:23][C:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:68])=[CH:60]2Participants
3
Procedure
The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nδ-trityl-L-glutaminyl]-3-hydroxy-4-methoxyaniline (605 mg, 0.8 mmol, example 109, step A) as described for example 109 (step B) using 5-fluoroindole-2-carboxylic acid (222 mg, 1.24 mmol) instead of N-(4-fluorobenzyl)indole-2-carboxylic acid. The crude material was purified by flash chromatography using 10, 20 and 40% EtOAc/CH2Cl2 as the eluent. The title compound was obtained as yellow crystals (400 mg, 72%).
Workup
- customThe crude material was purified by flash chromatography
Sources & evidence
- ORD record
- ord-d68d966a62594e84933a81b9b5d7a7f0
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06528655B1
Reaction notes
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