Water → Ethyl[8-chloro-1-(2-methoxyphenyl)-4-oxo-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl]acetate

HRID 1444828Notes

Reaction equation

HRID 1444828 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[CH2:6][C:7](=[O:19])[NH:8][CH2:9][CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].O>CN(C=O)C>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][N:8]1[CH2:9][CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[C:4]2[CH:3]=[C:2]([Cl:1])[CH:21]=[CH:20][C:5]=2[CH2:6][C:7]1=[O:19])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 590254937-Chloro-5-(2-methoxyphenyl)-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Product 1

HCID 59025538Ethyl[8-chloro-1-(2-methoxyphenyl)-4-oxo-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

254 mg of the compound from Example 21A (0.84 mol) are dissolved in 5 ml of DMF, and 549 mg of caesium carbonate (1.68 mol) and 190 μl of ethyl bromoacetate (281 mg, 1.68 mol) are added. The reaction mixture is stirred at room temperature overnight. 6 ml of water are added, and the mixture is extracted three times with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulphate. The solvent is removed in a rotary evaporator, and the residue is purified by preparative HPLC (eluent: acetonitrile/water, gradient 20:80→95:5). 254 mg (29% of theory) of the title compound are obtained.

Workup

  1. extractionthe mixture is extracted three times with dichloromethane
  2. washThe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customThe solvent is removed in a rotary evaporator
  5. customthe residue is purified by preparative HPLC (eluent: acetonitrile/water, gradient 20:80→95:5)

Sources & evidence

ORD record
ord-115e8e1ce6254bf893ec38ee83022f70
Source dataset
uspto-grants-2010_02
Patent number
US07662956B2

Reaction notes

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