Citric Acid → 8-acetoxy-4-(2-(diphenylmethoxy)ethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

HRID 2186726Notes

Reaction equation

HRID 2186726 reaction equation
[H-].[Na+].[C:3]([O:6][C:7]1[C:16]2[O:15][CH2:14][C:13](=[O:17])[NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)(=[O:5])[CH3:4].[C:18]1([CH:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:25][CH2:26][CH2:27]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.C1COCC1>[C:3]([O:6][C:7]1[C:16]2[O:15][CH2:14][C:13](=[O:17])[N:12]([CH2:27][CH2:26][O:25][CH:24]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1)(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 237821[(2-Bromoethoxy)(phenyl)methyl]benzeneHCID 224489418-acetoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 224489238-acetoxy-4-(2-(diphenylmethoxy)ethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazineYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous THF (15 ml) was added to sodium hydride (106 mg) to form a suspension, and a solution of 8-acetoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (498 mg) in anhydrous DMF (5 ml) was added to the resulting suspension, and the mixture was stirred at room temperature for 1 hour. 2-diphenylmethoxyethyl bromide (980 mg) was added to the mixture, and the mixture was stirred at room temperature overnight. The reaction solution was poured into a 3% citric acid aqueous solution, and then extracted with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over sodium sulfate, and then concentrated. The residue was purified by medium-pressure column chromatography (solvent:ethyl acetate/cyclohexane=1/3) to obtain the colorless oily object compound (640 mg, yield 66%).

Workup

  1. customto form a suspension
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe resultant organic layer was washed with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by medium-pressure column chromatography (solvent:ethyl acetate/cyclohexane=1/3)

Sources & evidence

ORD record
ord-281571eacdd646c58c0ef5f734e216a5
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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