Water → HCID 21349897, compound

HRID 2186749Notes

Reaction equation

HRID 2186749 reaction equation
[C:1]1([CH:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:8][C:9](=[O:23])[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-].[K+].[K+].Br[CH2:37][C:38]([O:40][CH3:41])=[O:39].O>CN(C=O)C>[C:24]1([CH:7]([NH:8][C:9]([CH2:10][N:11]2[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:15]=3[O:14][CH2:13][C:12]2=[O:22])=[O:23])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 22448916HCID 22448916, compound

Product 1

HCID 21349897HCID 21349897, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-diphenylmethyl-2-(8-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-4-yl)acetamide (735 mg) was dissolved in DMF (30 ml), and the resultant solution was stirred at room temperature. Potassium carbonate (785 mg) and methyl bromoacetate (0.35 ml) were added to the solution, and the mixture was stirred at room temperature for 18 hours. Water (25 ml) was added to the reaction solution, and the mixture was then extracted with ethyl acetate. The resultant organic layer was washed with saturated saline, dried over sodium sulfate, and concentrated. The resultant residue was recrystallized from ethyl acetate/n-hexane to obtain the object compound (492 mg, yield 56%)

Workup

  1. extractionthe mixture was then extracted with ethyl acetate
  2. washThe resultant organic layer was washed with saturated saline
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resultant residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-695e9dcce1664efa881331e6db35df39
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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