Potassium Carbonate → HCID 68536367, compound

HRID 2389363Notes

Reaction equation

HRID 2389363 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([NH:13][CH2:14][CH2:15][N:16]2[CH:21]=[C:20]([CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]=[CH:18][C:17]2=[O:35])=[O:12])[CH:6]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:23]1([CH:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:20]2[CH:19]=[CH:18][C:17](=[O:35])[N:16]([CH2:15][CH2:14][NH:13][C:11](=[O:12])[C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([OH:4])[CH:6]=3)[CH:21]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 68535578HCID 68535578, compound

Product 1

HCID 68536367HCID 68536367, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-[({2-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]ethyl}amino)carbonyl]phenyl acetate (77.0 mg) in MeOH (2.3 mL) was added portionwise K2CO3 (68.4 mg) at ambient temperature and the mixture was stirred at the same temperature for 15 minutes. The resulting mixture was diluted with water (5.0 mL) and the aqueous solution was extracted with EtOAc (10.0 mL). The organic layer was washed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to give N-{2-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]ethyl}-3-hydroxybenzamide (70 mg) as a off-white amorphous powder.

Workup

  1. extractionthe aqueous solution was extracted with EtOAc (10.0 mL)
  2. washThe organic layer was washed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution and brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-2ae72ecfa3a1406fb61e35661cb00e70
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

Loading…