Caffeic Acid → HCID 22976138, compound

HRID 1860334Notes

Reaction equation

HRID 1860334 reaction equation
C1C2C(CO[C:16]([NH:18][C@H:19]([C:31]([NH:33][CH2:34][CH2:35][C:36]3[CH:43]=[CH:42][C:40]([OH:41])=[C:38]([OH:39])[CH:37]=3)=[O:32])[CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])=[O:17])C3C(=CC=CC=3)C=2C=CC=1.C(O)(=O)/[CH:45]=[CH:46]/[C:47]1[CH:54]=[CH:53][C:51]([OH:52])=[C:49]([OH:50])[CH:48]=1>>[C:16]([NH:18][C@H:19]([C:31]([NH:33][CH2:34][CH2:35][C:36]1[CH:43]=[CH:42][C:40]([OH:41])=[C:38]([OH:39])[CH:37]=1)=[O:32])[CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])(=[O:17])/[CH:45]=[CH:46]/[C:47]1[CH:54]=[CH:53][C:51]([OH:52])=[C:49]([OH:50])[CH:48]=1

Participants

3

Reactant 2

HCID 689043Caffeic AcidHCID 22976124HCID 22976124, compound

Product 1

HCID 22976138HCID 22976138, compound

Procedure

N-[Nα-(9-fluorenylmethoxycarbonyl)-Nδ-butoxycarbonyl-L-ornithyl]dopamine (1.0 g, 1.75 mmol) was deprotected following the indications of general procedure G. The free amino groups thus obtained were coupled with caffeic acid (472 mg, 2.6 mmol) following the general procedure D. The crude material was purified by flash chromatography using a solvent gradient from 30% to 90% EtOAc/CH2Cl2/1% AcOH. The desired product was obtained as white crystals (370 mg, 40%).

Workup

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

Sources & evidence

ORD record
ord-66476d8ab3804f839fc0add0013ac444
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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