N-(5-tert-Butoxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide → N-(5-Hydroxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide

HRID 1830407Notes

Reaction equation

HRID 1830407 reaction equation
C([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:40])[C:16]2[CH:21]=[C:20]([CH2:22][C:23]3[C:24](=[O:35])[C:25]([O:33][CH3:34])=[C:26]([O:31][CH3:32])[C:27](=[O:30])[C:28]=3[CH3:29])[CH:19]=[CH:18][C:17]=2[O:36][C:37](=[O:39])[CH3:38])=[N:12][CH:13]=1)=[O:7])(C)(C)C>C(O)=O>[OH:7][C:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:40])[C:16]2[CH:21]=[C:20]([CH2:22][C:23]3[C:24](=[O:35])[C:25]([O:33][CH3:34])=[C:26]([O:31][CH3:32])[C:27](=[O:30])[C:28]=3[CH3:29])[CH:19]=[CH:18][C:17]=2[O:36][C:37](=[O:39])[CH3:38])=[N:12][CH:13]=1)=[O:5]

Participants

3

Reactant 1

HCID 22054129N-(5-tert-Butoxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide

Product 1

HCID 22054147N-(5-Hydroxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

N-(5-tert-Butoxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide (0.170 g, 0.309 mmol) was dissolved in formic acid (3.0 ml) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was concentrated and the obtained residue was purified by silica gel chromatography (chloroform:methanol=10:1) and then recrystallized from ether to obtain the titled compound (0.109 g, 0.220 mmol, 71%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe obtained residue was purified by silica gel chromatography (chloroform:methanol=10:1)
  3. customrecrystallized from ether

Sources & evidence

ORD record
ord-9abd715531ab41079eafc0fef6727a3f
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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