Indole-2-carboxylic acid → (2S)-N-(2,5-dimethoxyphenyl)-2-(1H-indole-2-carbonylamino)-N'-trityl-pentanediamide

HRID 1860341Notes

Reaction equation

HRID 1860341 reaction equation
C1C2C(COC([NH:18][C@H:19]([C:44]([NH:46][C:47]3[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:48]=3[O:55][CH3:56])=[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.[NH:57]1[C:65]2[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=2)[CH:59]=[C:58]1[C:66]([OH:68])=O>>[NH:57]1[C:65]2[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=2)[CH:59]=[C:58]1[C:66]([NH:18][C@H:19]([C:44]([NH:46][C:47]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:48]=1[O:55][CH3:56])=[O:45])[CH2:20][CH2:21][C:22](=[O:43])[NH:23][C:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:68]

Participants

3

Reactant 2

HCID 72899Indole-2-carboxylic acidHCID 22976128N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ndelta-trityl-L-glutaminyl]-2,5-dimethoxyaniline

Product 1

HCID 504849(2S)-N-(2,5-dimethoxyphenyl)-2-(1H-indole-2-carbonylamino)-N'-trityl-pentanediamide

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nδ-trityl-L-glutaminyl]-2,5-dimethoxyaniline (620 mg, 0.83 mmol, example 82, step A) as described for example 82 (step B) using indole-2-carboxylic acid (201 mg, 1.25 mmol) instead of caffeic acid. The crude material was purified by flash chromatography using initially 10% then 20% EtOAc/CH2Cl2. The title compound was obtained as white crystals (200 mg, 36%).

Workup

  1. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-7bf6114d30364d3395fc1ce718dee25a
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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