Sodium Bicarbonate → HCID 22054288, compound

HRID 1830351Notes

Reaction equation

HRID 1830351 reaction equation
C(=O)([O-])O.[Na+].[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:38])[C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]3[C:22](=[O:33])[C:23]([O:31][CH3:32])=[C:24]([O:29][CH3:30])[C:25](=[O:28])[C:26]=3[CH3:27])=[CH:16][C:15]=2[O:34]C(=O)C)[CH:7]=1>CO>[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:38])[C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]3[C:22](=[O:33])[C:23]([O:31][CH3:32])=[C:24]([O:29][CH3:30])[C:25](=[O:28])[C:26]=3[CH3:27])=[CH:16][C:15]=2[OH:34])[CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054135HCID 22054135, compound

Product 1

HCID 22054288HCID 22054288, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous saturated sodium hydrogencarbonate solution (4 ml) was added to a methanol solution (10 ml) of N-(pyridin-3-yl)-4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide (55 mg, 0.122 mmol) and the resulting solution was stirred for 1 hour. The reaction solution was extracted with ethyl acetate, then washed with water and dried, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (benzene:acetone=3:1) to obtain the titled compound (28 mg, 0.0686 mmol, 56%).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washwashed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe residue was purified by silica gel column chromatography (benzene:acetone=3:1)

Sources & evidence

ORD record
ord-1ae0a441c7a1447aa4793cfaa50019f7
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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