Water → HCID 54220897, compound

HRID 2186734Notes

Reaction equation

HRID 2186734 reaction equation
[C:1]([O:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][C:14](=[O:16])[NH:15][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26].O>CN(C=O)C>[C:1]([O:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][C:14](=[O:16])[N:15]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 22448959HCID 22448959, compound

Product 1

HCID 54220897HCID 54220897, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-acetoxy-2-oxo-2,3,4,5-tetrahydro-1H-1-benzoazepine (252 mg) was dissolved in DMF (5 ml), and the resultant solution was stirred at room temperature. Potassium carbonate (509 mg) and methyl bromoacetate (0.22 ml) were added to the solution at room temperature. After disappearance of the raw materials was confirmed, water (20 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 anhydrous sodium sulfate, and then concentrated. The resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=1/1) to obtain the object compound ml (333 mg, yield 99%).

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 anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=1/1)
  6. customto obtain the object compound ml (333 mg, yield 99%)

Sources & evidence

ORD record
ord-09dac0ae9ab742eba3b8a13cb01910fd
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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