3-(2,5-Dimethoxyphenyl)-2-propenoic acid → N-[Nalpha-(2,5-Dimethoxycinnamoyl)-O-tert-butyl-L-seryl]dopamine

HRID 1860331Notes

Reaction equation

HRID 1860331 reaction equation
C1C2C(CO[C:16]([NH:18][C@H:19]([C:26]([NH:28][CH2:29][CH2:30][C:31]3[CH:38]=[CH:37][C:35]([OH:36])=[C:33]([OH:34])[CH:32]=3)=[O:27])[CH2:20][O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:17])C3C(=CC=CC=3)C=2C=CC=1.[CH3:39][O:40][C:41]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][C:42]=1[CH:43]=[CH:44]C(O)=O>>[CH3:39][O:40][C:41]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][C:42]=1[CH:43]=[CH:44][C:16]([NH:18][C@H:19]([C:26]([NH:28][CH2:29][CH2:30][C:31]1[CH:38]=[CH:37][C:35]([OH:36])=[C:33]([OH:34])[CH:32]=1)=[O:27])[CH2:20][O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:17]

Participants

3

Reactant 2

HCID 1145783-(2,5-Dimethoxyphenyl)-2-propenoic acidHCID 22976135N-[Nalpha-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamine

Product 1

HCID 504809N-[Nalpha-(2,5-Dimethoxycinnamoyl)-O-tert-butyl-L-seryl]dopamine

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamine (572 mg, 1.1 mmol, example 42, step A) as described for example 42 (step B) using 2,5-dimethoxycinnamic acid (345 mg, 1.7 mmol) instead of caffeic acid. The crude material was purified by flash chromatography using 10% EtOAc/CH2Cl2/1% AcOH and 50% EtOAc/CH2Cl2 as the eluent. The title compound was obtained as a yellow powder (300 mg, 56%).

Workup

  1. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-1acbf86edf554d15b263eb2bd0ce5434
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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