Gallic Acid → N-[(1S)-1-(tert-butoxymethyl)-2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxo-ethyl]-3,4,5-trihydroxy-benzamide

HRID 1860330Notes

Reaction equation

HRID 1860330 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.C(O)(=O)[C:40]1[CH:48]=[C:46]([OH:47])[C:44]([OH:45])=[C:42]([OH:43])[CH:41]=1>>[OH:43][C:42]1[CH:41]=[C:40]([CH:48]=[C:46]([OH:47])[C:44]=1[OH:45])[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 370Gallic AcidHCID 22976135N-[Nalpha-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamine

Product 1

HCID 504808N-[(1S)-1-(tert-butoxymethyl)-2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxo-ethyl]-3,4,5-trihydroxy-benzamide

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamine (1.16 g, 2.24 mmol, example 42, step A) as described for example 42 (step B) using gallic acid (571 mg, 3.36 mmol) instead of caffeic acid. The crude material was purified by flash chromatography using successively 30%, 40% and 70% EtOAc/CH2Cl2/1% AcOH as the eluent. The title compound was obtained as a white powder (300 mg, 30%).

Workup

  1. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-80ae7aeb7de9401a8db9e0b1e4472a9c
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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