Protocatechuic Acid → N-[Nalpha-(3,4-Dihydroxybenzoyl)-Ndelta-methyltrityl-L-glutaminyl]-3,4-dihydroxybenzylamine

HRID 1860327Notes

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

Participants

Reactant 2

HCID 72Protocatechuic Acid

HCID 22976126N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ndelta-methyltrityl-L-glutaminyl]-3,4-dihydroxybenzylamine

Product 1

HCID 22976105N-[Nalpha-(3,4-Dihydroxybenzoyl)-Ndelta-methyltrityl-L-glutaminyl]-3,4-dihydroxybenzylamine

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nδ-methyltrityl-L-glutaminyl]-3,4-dihydroxybenzylamine (576 mg, 0.8 mmol, example 26, step A) as described for example 26 (step B) using 3,4-dihydroxybenzoic acid (178 mg, 1.2 mmol) instead of 4-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 white crystals (190 mg, 32%).

Workup

customThe crude material was purified by flash chromatography

Sources & evidence

ORD record: ord-3ab5baddd985487287a452c8b2659a15
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528655B1

Reaction notes

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