Ethyl bromoacetate → HCID 59145214, compound

HRID 2389384Notes

Reaction equation

HRID 2389384 reaction equation
[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:26])[N:12]([CH2:14][CH2:15][NH:16][C:17](=[O:25])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=3)[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]>CN(C=O)C.O>[C:1]1([CH:7]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:26])[N:12]([CH2:14][CH2:15][NH:16][C:17]([C:18]3[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=3)[O:24][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[O:25])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 68536367HCID 68536367, compound

Product 1

HCID 59145214HCID 59145214, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of N-{2-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]ethyl}-3-hydroxybenzamide (60.0 mg) and K2CO3 (58.6 mg) in DMF (1.8 mL) was added dropwise ethyl bromoacetate (18.8 μL) at ambient temperature and the mixture was stirred at the same temperature for 14 hours. 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. The residue was purified by silica gel column chromatography (chloroform:MeOH=98:2) to give ethyl {3-[({2-[5-(diphenylmethyl)-2-oxo-1(2H) -pyridinyl]ethyl}amino)carbonyl]phenoxy}acetate (70 mg) as a colorless syrup.

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
  6. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=98:2)

Sources & evidence

ORD record
ord-637ce1f71f704c0cb1ede2095e714d69
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

Loading…