Potassium Carbonate → HCID 86758191, compound

HRID 2186747Notes

Reaction equation

HRID 2186747 reaction equation
[C:1]1([C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH3:23])[CH2:8][CH2:9][CH2:10][N:11]2[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([OH:21])[C:15]=3[O:14][CH2:13][C:12]2=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-:31].[K+].[K+].Br[CH2:37][C:38]([O:40][CH3:41])=[O:39].[Cl-].[NH4+]>CN(C=O)C>[C:24]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH3:23])[CH2:8][CH2:9][CH2:10][N:11]2[C:16]3[CH:17]=[CH:18][CH2:19][C:20]([OH:31])([O:21][CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:15]=3[O:14][CH2:13][C:12]2=[O:22])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 21349852HCID 21349852, compound

Product 1

HCID 86758191HCID 86758191, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4,4-diphenylpentyl)-8-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine was dissolved in anhydrous DMF (15 ml), and anhydrous potassium carbonate (180 mg) and methyl bromoacetate (0.15 ml) were added to the resultant solution, and the mixture was stirred at room temperature overnight. The reaction solution was poured into a saturated ammonium chloride aqueous solution, and then extracted with ethyl acetate containing 15% n-hexane. The resultant organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated. The resultant residue was purified by medium-pressure column chromatography (solvent:ethyl acetate/cyclohexane=1/3) to obtain the colorless oily object compound (386 mg, yield 92%).

Workup

  1. extractionextracted with ethyl acetate containing 15% n-hexane
  2. washThe resultant organic layer was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resultant residue was purified by medium-pressure column chromatography (solvent:ethyl acetate/cyclohexane=1/3)

Sources & evidence

ORD record
ord-30be33324cf24354b673b2992c90124c
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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