Sodium Bicarbonate → HCID 22054197, compound

HRID 1830349Notes

Reaction equation

HRID 1830349 reaction equation
C(=O)([O-])O.[Na+].[CH3:6][O:7][C:8]1[C:9](=[O:45])[C:10]([CH3:44])=[C:11]([CH2:17][C:18]2[CH:39]=[CH:38][C:21]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])=[CH:27][CH:26]=3)=[O:23])=[C:20]([O:40]C(=O)C)[CH:19]=2)[C:12](=[O:16])[C:13]=1[O:14][CH3:15]>CO>[CH3:6][O:7][C:8]1[C:9](=[O:45])[C:10]([CH3:44])=[C:11]([CH2:17][C:18]2[CH:39]=[CH:38][C:21]([C:22]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([S:31]([C:34]([F:35])([F:36])[F:37])(=[O:32])=[O:33])=[CH:29][CH:30]=3)=[O:23])=[C:20]([OH:40])[CH:19]=2)[C:12](=[O:16])[C:13]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054335HCID 22054335, compound

Product 1

HCID 22054197HCID 22054197, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous saturated sodium hydrogencarbonate solution (7 ml) was added to a methanol solution (15 ml) of N-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-(trifluoromethylsulfonyl)aniline (114 mg, 0.196 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 (hexand:ethyl acetate=4:1) to obtain the titled compound (35 mg, 0.065 mmol, 33%).

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 (hexand:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-51042004adc8458180a0d48bc7361081
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

Loading…