Sodium Hydroxide → Rabeprazole

HRID 226229

반응식

HRID 226229 반응식
[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]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 9949996Rabeprazole-thioether

생성물 1

HCID 5029Rabeprazole수율 23.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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; 5.37 g (21.8 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 (14 ml) and acetonitrile (92 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylsulfinyl]-1H-benzimidazole (6.26 g) (HPLC purity 99.7%, yield 23.9%).

후처리

  1. temperaturethe solution was cooled
  2. additionmcpba (70.2% purity; 5.37 g (21.8 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

출처 및 근거

ORD 기록
ord-462f2b5023cf429798e5620258708ca0
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557217B2

연결된 노트

불러오는 중…