Sodium Hydroxide → Rabeprazole

HRID 226231

反応式

HRID 226231 の反応式
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[C:8]=1[CH3:24].[OH-:25].[Na+]>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14]([C:15]2[NH:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[O:25])[C:8]=1[CH3:24]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 9949996Rabeprazole-thioether

生成物 1

HCID 5029Rabeprazole収率 32.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-[{4-(3-Methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (25.0 g (72.8 mmol)) was dissolved in dichloromethane, and then the solution was cooled, and mcpba (70.2% purity; 7.16 g (29.1 mmol)) was added little by little such that the internal temperature did not exceed −15° C. After the addition, a 10% sodium hydroxide aqueous solution (70.8 ml) was added, the mixture was stirred and then left to stand, and then the aqueous layer was separated off. The separated aqueous layer was washed twice with dichloromethane (48 ml). A 2N ammonium acetate aqueous solution was then put into the solution, and then extraction was carried out twice with dichloromethane (48 ml). The dichloromethane layers were washed twice with water (48 ml), vacuum concentration was carried out, crystallization was carried out using dichloromethane (18 ml) and acetone (120 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylsulfinyl]-1H-benzimidazole (8.56 g) (HPLC purity 99.7%, yield 32.7%).

後処理

  1. temperaturethe solution was cooled
  2. additionmcpba (70.2% purity; 7.16 g (29.1 mmol)) was added little by little such that the internal temperature
  3. customdid not exceed −15° C
  4. additionAfter the addition
  5. waitleft
  6. customthe aqueous layer was separated off
  7. washThe separated aqueous layer was washed twice with dichloromethane (48 ml)
  8. extractionextraction
  9. washThe dichloromethane layers were washed twice with water (48 ml), vacuum concentration
  10. customcrystallization
  11. filtrationfiltration

出典と根拠

ORDレコード
ord-b86614672aa140db9f3fd87d50335ade
出典データセット
uspto-grants-2009_07
特許番号
US07557217B2

関連ノート

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