N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ndelta-trityl-L-glutaminyl]-2,5-dimethoxyaniline → HCID 178492603, compound

HRID 1860342Notes

Reaction equation

HRID 1860342 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.[OH:57][C:58]1[C:67]2[C:62](=[C:63]([OH:68])[CH:64]=[CH:65][CH:66]=2)[N:61]=[C:60]([C:69]([OH:71])=O)[CH:59]=1>>[OH:57][C:58]1[C:67]2[C:62](=[C:63]([OH:68])[CH:64]=[CH:65][CH:66]=2)[N:61]=[C:60]([C:69]([NH:18][C@H:19]([C:44]([NH:46][C:47]2[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:48]=2[O:55][CH3:56])=[O:45])[CH2:20][CH2:21][C:22](=[O:43])[NH:23][C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:71])[CH:59]=1

Participants

3

Reactant 2

HCID 22976128N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ndelta-trityl-L-glutaminyl]-2,5-dimethoxyanilineHCID 1785245884,8-dihydroxyquinoline-2-carboxylic acid

Product 1

HCID 178492603HCID 178492603, compound

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nδ-trityl-L-glutaminyl]-2,5-dimethoxyaniline (703 mg, 0.94 mmol, example 82, step A) as described for example 82 (step B) using 4,8-dihydroxyquinoline-2-carboxylic acid (291 mg, 1.42 mmol) instead of caffeic acid. The crude material was purified by flash chromatography using initially 20% then 50% EtOAc/CH2Cl2. The title compound was obtained as white crystals (150 mg, 22%).

Workup

  1. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-7378dba2bf994f3ab262ec73f8da8d33
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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