HCID 22054278, compound → HCID 22054240, compound

HRID 1830404Notes

Reaction equation

HRID 1830404 reaction equation
C([O:5][C:6]([C:8]1[C:9]([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:10][CH:11]=[CH:12][CH:13]=1)=[O:7])(C)(C)C>C(O)=O>[OH:7][C:6]([C:8]1[C:9]([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:10][CH:11]=[CH:12][CH:13]=1)=[O:5]

Participants

3

Reactant 1

HCID 22054278HCID 22054278, compound

Product 1

HCID 22054240HCID 22054240, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

N-(3-tert-Butoxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide (0.140 g, 0.254 mmol) was dissolved in formic acid (2.0 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 (0.110 g, 0.222 mmol, 87%).

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-b7133646a2894529801507f3832e5350
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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