Caffeic Acid → HCID 6478499, compound

HRID 1860326Notes

Reaction equation

HRID 1860326 reaction equation
[C:1]([NH:13][C@H:14]([C:29]([NH:31][CH2:32][CH2:33][C:34]1[CH:41]=[CH:40][C:38]([OH:39])=[C:36]([OH:37])[CH:35]=1)=[O:30])[CH2:15][CH2:16][CH2:17][NH:18]C(OCC1C=CC=CC=1)=O)(=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1.[C:42]([OH:54])(=O)/[CH:43]=[CH:44]/[C:45]1[CH:52]=[CH:51][C:49]([OH:50])=[C:47]([OH:48])[CH:46]=1>>[C:1]([NH:13][C@H:14]([C:29]([NH:31][CH2:32][CH2:33][C:34]1[CH:41]=[CH:40][C:38]([OH:39])=[C:36]([OH:37])[CH:35]=1)=[O:30])[CH2:15][CH2:16][CH2:17][NH:18][C:42](=[O:54])/[CH:43]=[CH:44]/[C:45]1[CH:52]=[CH:51][C:49]([OH:50])=[C:47]([OH:48])[CH:46]=1)(=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1

Participants

3

Reactant 2

HCID 689043Caffeic AcidHCID 22976137HCID 22976137, compound

Product 1

HCID 6478499HCID 6478499, compound

Procedure

N-(Nα-caffeoyl-Nδ-benzyloxycarbonyl-L-ornithyl)dopamine (1.3 g, 2.6 mmol) was completely deprotected following the indications of general procedures E and C. The free amino groups thus obtained were coupled with caffeic acid (1.2 g, 6.4 mmol) following the general procedure G. The crude material was purified by flash chromatography using a solvent gradient from 50% to 90% EtOAc/CH2Cl2/1% AcOH and 5% MeOH/EtOAc/1% AcOH. The desired product was obtained as yellow crystals (300 mg, 25%).

Workup

  1. customThe free amino groups thus obtained
  2. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-0058afb2312f4163b7c08a56b1f477bb
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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