Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 7-(2-Chloroethoxy)-alpha-(cyclohexylthio)-alpha-(3,4-dimethoxyphenyl)-3,4-dihydro-6-methoxy-2(1H)-isoquinolineheptanonitrile

HRID 274022ノート

反応式

HRID 274022 の反応式
[CH:1]1([S:7][C:8]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=2)([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]([OH:28])=[C:21]([O:26][CH3:27])[CH:22]=3)[CH2:17]2)[C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[Cl:41][CH2:42][CH2:43]OS(C1C=CC(C)=CC=1)(=O)=O>CC(=O)CC>[Cl:41][CH2:42][CH2:43][O:28][C:20]1[CH:19]=[C:18]2[C:23]([CH2:24][CH2:25][N:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:8]([S:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=3)[C:9]#[N:10])[CH2:17]2)=[CH:22][C:21]=1[O:26][CH3:27]

参加物

5

反応物 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 14798Sodium HydroxideHCID 10650088alpha-(Cyclohexylthio)-alpha-(3,4-dimethoxyphenyl)-3,4-dihydro-7-hydroxy-6-methoxy-2(1H)-isoquinolineheptanenitrile

生成物 1

HCID 105794917-(2-Chloroethoxy)-alpha-(cyclohexylthio)-alpha-(3,4-dimethoxyphenyl)-3,4-dihydro-6-methoxy-2(1H)-isoquinolineheptanonitrile

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

A mixture, under argon, of 2.0 g of product from Example 114, 15 ml of 1N sodium hydroxide, 5.4 ml of 2-chloroethyl-p-toluene sulfonate and 70 ml of 2-butanone is heated at reflux temperature for 18 hours. The mixture is cooled, concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic layer is washed with saturated sodium chloride, dried, and concentrated in Vacuo to give an oil. The oil is purified by chromatography (silica gel: methylene chloride, 0.5%, 1.0% and 1.5% methyl alcohol/methylene chloride) to give 1.7 g of the desired product.

後処理

  1. temperatureat reflux temperature for 18 hours
  2. temperatureThe mixture is cooled
  3. concentrationconcentrated in vacuo
  4. customthe residue partitioned between ethyl acetate and water
  5. washThe organic layer is washed with saturated sodium chloride
  6. customdried
  7. concentrationconcentrated in Vacuo
  8. customto give an oil
  9. customThe oil is purified by chromatography (silica gel: methylene chloride, 0.5%, 1.0% and 1.5% methyl alcohol/methylene chloride)

出典と根拠

ORDレコード
ord-7a097c936f0d439aaca014a8c66ca933
出典データセット
uspto-grants-1995_02
特許番号
US05387685

反応ノート

読み込み中…