Acetone → HCID 66990532, compound

HRID 454620Notes

Reaction equation

HRID 454620 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[CH:12]=[CH:13][C:14]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[C:15]([CH:35]=1)[C:16]([NH:18][C:19]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])=[O:17])(=O)C.CC(C)=O>C(Cl)(Cl)Cl.CO>[CH2:37]([O:36][C:14]1[CH:13]=[CH:12][C:11]([OH:10])=[CH:35][C:15]=1[C:16]([NH:18][C:19]1[CH:28]=[C:27]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])=[O:17])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 66990305HCID 66990305, compound

Product 1

HCID 66990532HCID 66990532, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Potassium carbonate (1.6 g) was added to a solution mixture of methyl 2-(5-acetoxy-2-(benzyloxy)benzamido)-4-phenylbenzoate (3.8 g) in chloroform (5.0 mL), methanol (10 mL), and acetone (10 mL), followed by stirring at room temperature for 1 hour. The insoluble substance was removed by filtration, and then the solvent was evaporated under reduced pressure, and 1.0 mol/L hydrochloric acid and chloroform were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 3.4 g of methyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate as a white solid.

Workup

  1. customThe insoluble substance was removed by filtration
  2. customthe solvent was evaporated under reduced pressure, and 1.0 mol/L hydrochloric acid and chloroform
  3. additionwere added to the residue
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-da3fb04868be446a8eda29e625185d80
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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