Sodium Hydroxide → Rabeprazole

HRID 226234

Reaktionsgleichung

Reaktionsgleichung von HRID 226234
[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]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 9949996Rabeprazole-thioether

Produkt 1

HCID 5029RabeprazoleAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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; 8.95 g (36.4 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 acetone (165 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylsulfinyl]-1H-benzimidazole (10.8 g) (HPLC purity 99.6%, yield 41.4%).

Aufarbeitung

  1. temperaturethe solution was cooled
  2. additionmcpba (70.2% purity; 8.95 g (36.4 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

Quellen und Nachweise

ORD-Eintrag
ord-43f4dd644df84f21a7db87b492a29776
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557217B2

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