Diltiazem → cis-3-(Acetyloxy)-2,3,4,5-tetrahydro-2-(4-methoxyphenyl)-N-[2-(3,5-dimethoxyphenyl)ethyl]-N,N-dimethyl-4-oxo-1,5-benzothiazepine-5-ethanaminium iodide

HRID 568784ノート

反応式

HRID 568784 の反応式
[CH3:1][C:2]([O:4][C@H:5]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:7][C@H:6]1[C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)=[O:3].[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([O:41][CH3:42])[CH:40]=1)[CH2:35][CH2:36][I:37]>CCOC(C)=O>[I-:37].[C:2]([O:4][C@H:5]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][N+:19]([CH2:36][CH2:35][C:34]2[CH:38]=[C:39]([O:41][CH3:42])[CH:40]=[C:32]([O:31][CH3:30])[CH:33]=2)([CH3:21])[CH3:20])[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:7][C@H:6]1[C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)(=[O:3])[CH3:1]

参加物

4

反応物 2

HCID 39186DiltiazemHCID 126839771-(2-Iodoethyl)-3,5-dimethoxybenzene

生成物 1

HCID 67937049cis-3-(Acetyloxy)-2,3,4,5-tetrahydro-2-(4-methoxyphenyl)-N-[2-(3,5-dimethoxyphenyl)ethyl]-N,N-dimethyl-4-oxo-1,5-benzothiazepine-5-ethanaminium iodide収率 63.7%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a flask under nitrogen was added 5.0 g (0.0121 mole) of diltiazem, 3.52 g (0.0121 mole) of 3,5-dimethoxyphenethyl iodide, and 20 ml of EtOAc. The reaction mixture was heated at 50° C. for 24 hr then at 75° C. for 97 hr. The reaction was cooled to RT, the solvent decanted, and the oily residue washed three times with EtOAc. The oily residue was dissolved in methylene chloride, washed with water and dried over MgSO4. The solvent was evaporated to give 5.45 g of a mixture of the title product and diltiazem hydroiodide as a tan foam.

後処理

  1. temperatureThe reaction was cooled to RT
  2. customthe solvent decanted
  3. washthe oily residue washed three times with EtOAc
  4. dissolutionThe oily residue was dissolved in methylene chloride
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-5867a41daf9544d99acdef383e874dc3
出典データセット
uspto-grants-1988_03
特許番号
US04729994

反応ノート

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