Caffeic Acid → HCID 22976143, compound

HRID 1860325Notes

Reaction equation

C(OC([NH:8][C@H:9]([C:20]([NH:22][CH2:23][CH2:24][C:25]1[CH:32]=[CH:31][C:29]([OH:30])=[C:27]([OH:28])[CH:26]=1)=[O:21])[C@@H:10]([CH3:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)(C)(C)C.[C:33]([OH:45])(=O)/[CH:34]=[CH:35]/[C:36]1[CH:43]=[CH:42][C:40]([OH:41])=[C:38]([OH:39])[CH:37]=1>>[C:33]([NH:8][C@H:9]([C:20]([NH:22][CH2:23][CH2:24][C:25]1[CH:32]=[CH:31][C:29]([OH:30])=[C:27]([OH:28])[CH:26]=1)=[O:21])[C@@H:10]([CH3:19])[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:45])/[CH:34]=[CH:35]/[C:36]1[CH:43]=[CH:42][C:40]([OH:41])=[C:38]([OH:39])[CH:37]=1

Participants

Reactant 2

HCID 689043Caffeic Acid

HCID 22976153HCID 22976153, compound

Product 1

HCID 22976143HCID 22976143, compound

Procedure

The title compound was prepared from N-[Nα-(tert-butoxycarbonyl)-O-benzyl-L-threonyl]dopamine (1.0 g, 2.3 mmol, example 9, step A) as described for example 9 (step B) using caffeic acid (620 mg, 3.4 mmol) instead of 3,4-dihydroxybenzoic acid. The crude material was purified by flash chromatography using 30% EtOAc/CHCl3 and 5% MeOH/CHCl3 as the eluent. The title compound was obtained as yellow crystals (717 mg, 62%).

Workup

customThe crude material was purified by flash chromatography

Sources & evidence

ORD record: ord-56e5e931c4514f60a1ee44c27ef8ec49
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528655B1

Reaction notes

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