N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ndelta-methyltrityl-L-glutaminyl]-3,4-dihydroxybenzylamine → HCID 178485711, compound

HRID 1860337Notes

Reaction equation

HRID 1860337 reaction equation
C1C2C(COC([N:18]([C:38]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@H:19]([C:26]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([OH:37])[CH:31]=3)=[O:27])[CH2:20][CH2:21][C:22](=[O:25])[NH:23][CH3:24])=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]([N:18]([C:38]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C@H:19]([C:26]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([OH:37])[CH:31]=2)=[O:27])[CH2:20][CH2:21][C:22](=[O:25])[NH:23][CH3:24])=[O:71])[CH:59]=1

Participants

3

Reactant 2

HCID 22976126N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ndelta-methyltrityl-L-glutaminyl]-3,4-dihydroxybenzylamineHCID 1785245884,8-dihydroxyquinoline-2-carboxylic acid

Product 1

HCID 178485711HCID 178485711, compound

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nδ-methyltrityl-L-glutaminyl]-3,4-dihydroxybenzylamine (1.0 g, 1.4 mmol, example 26, step A) as described for example 26 using 4,8-dihydroxyquinoline-2-carboxylic acid (435 mg, 2.1 mmol) instead of4-hydroxy-3-nitrobenzoic acid. The crude material was purified by flash chromatography using a solvent gradient from 30% to 60% EtOAc/CH2Cl2/1% AcOH. The title compound was obtained as yellow crystals (100 mg, 10%).

Workup

  1. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-0384969eeeb044bf8e1766930b5e90e8
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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