Protocatechuic Acid → (2S)-2-[(3,4-dihydroxybenzoyl)amino]-N-[2-(3,4-dihydroxyphenyl)ethyl]-N'-trityl-butanediamide

HRID 1860323Notes

Reaction equation

C1C2C(CO[C:16]([NH:18][C@H:19]([C:43]([NH:45][CH2:46][CH2:47][C:48]3[CH:55]=[CH:54][C:52]([OH:53])=[C:50]([OH:51])[CH:49]=3)=[O:44])[CH2:20][C:21](=[O:42])[NH:22][C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:17])C3C(=CC=CC=3)C=2C=CC=1.[OH:56][C:57]1[CH:58]=[C:59]([CH:63]=[CH:64][C:65]=1[OH:66])C(O)=O>>[OH:56][C:57]1[CH:58]=[C:59]([CH:63]=[CH:64][C:65]=1[OH:66])[C:16]([NH:18][C@H:19]([C:43]([NH:45][CH2:46][CH2:47][C:48]1[CH:55]=[CH:54][C:52]([OH:53])=[C:50]([OH:51])[CH:49]=1)=[O:44])[CH2:20][C:21](=[O:42])[NH:22][C:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:17]

Participants

Reactant 2

HCID 72Protocatechuic Acid

HCID 22976130N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ngamma-trityl-L-asparagyl]dopamine

Product 1

HCID 504775(2S)-2-[(3,4-dihydroxybenzoyl)amino]-N-[2-(3,4-dihydroxyphenyl)ethyl]-N'-trityl-butanediamide

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nγ-trityl-L-asparagyl]dopamine (1.3 g, 1.7 mmol, example 7, step A) as described for example 7 (step B) using 3,4-dihydroxybenzoic acid (402 mg, 2.6 mmol) instead of caffeic acid. The crude material was purified by flash chromatography using a solvent gradient from 30% to 60% EtOAc/CH2Cl2 containing 1% AcOH. The title compound was obtained as white crystals (579 mg, 52%).

Workup

customThe crude material was purified by flash chromatography

Sources & evidence

ORD record: ord-632713bbb1ca4994be14336b02018e90
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528655B1

Reaction notes

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