Water → Lansoprazole

HRID 1829904Notes

Reaction equation

HRID 1829904 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].CC([O:29]O)(C)C.O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(O)C>[CH3:1][C:2]1[C:7]([O:8][CH2:9][C:10]([F:12])([F:11])[F:13])=[CH:6][CH:5]=[N:4][C:3]=1[CH2:14][S+:15]([O-:29])[C:16]1[NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6410tert-Butyl hydroperoxideHCID 1094080Lansoprazole sulfide

Product 1

HCID 3883LansoprazoleYield 37%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 3776IsopropanolSolvent

Procedure

At room temperature, 1.307 g of 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methylthio]-1H-benzimidazole, 0.059 g of tetrabutyl ammonium bromide as an interphase transfer catalyst, and 0.157 g of Mo(acac)2 oxidation catalyst were mixed in 15 ml of IPA. Next, 1.36 g of TBHP (70% aqueous solution) was added into the mixture in about 5–10 minutes. The reaction was carried out for about 30 hours, and then 60 ml of water was added, and the reaction was continued for another one hour while stirring. Finally, the precipitate formed was filtered, water washed, and dried to obtain Lansoprazole with a yield of about 37% (HPLC purity>96%).

Workup

  1. waitthe reaction was continued for another one hour
  2. customFinally, the precipitate formed
  3. filtrationwas filtered
  4. washwater washed
  5. customdried

Sources & evidence

ORD record
ord-5e41d8e33c864c9e8167e1a3b783c123
Source dataset
uspto-grants-2006_06
Patent number
US07064213B1

Reaction notes

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