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

HRID 1444828ノート

反応式

HRID 1444828 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-115e8e1ce6254bf893ec38ee83022f70
出典データセット
uspto-grants-2010_02
特許番号
US07662956B2

反応ノート

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