Acetic Acid → Lansoprazole

HRID 492142Notes

Reaction equation

HRID 492142 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].[O-:25]S([O-])(=S)=O.[Na+].[Na+].C(O)(=O)C>C(O)C.OO.O>[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-:25])[C:16]1[NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 24477Sodium ThiosulfateHCID 1094080Lansoprazole sulfide

Product 1

HCID 3883LansoprazoleYield 63%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 784Hydrogen PeroxideSolventHCID 962WaterSolvent

Procedure

0.5 g of 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]thio]-1H-benzimidazole was suspended in 7 ml of ethanol at room temperature. 0.025 g of Na2WO4·2H2O oxidation catalyst was dissolved in 0.141 g H2O2 (35% aqueous solution), and further diluted with 2 ml of water. The oxidant/catalyst solution was added to the reactant suspension dropwise so that the addition was completed in about 30 minutes while stirring at room temperature. The reaction was continued for additional 8 hours while stirring. 2 ml of 10% Na2S2O3 aqueous solution was then added, and the resulting mixture was subjected to a reduced pressure to remove ethanol therefrom. Finally, a precipitate was formed after adding a diluted acetic acid aqueous solution to a pH value of about 8, which was filtered, water washed, and dried in vacuo to obtain Lansoprazole with a yield of about 63% (LC purity>80%).

Workup

  1. additionThe oxidant/catalyst solution was added to the reactant suspension dropwise so that the addition
  2. waitThe reaction was continued for additional 8 hours
  3. stirringwhile stirring
  4. customto remove ethanol
  5. customFinally, a precipitate was formed
  6. filtrationwas filtered
  7. washwater washed
  8. customdried in vacuo

Sources & evidence

ORD record
ord-b57c6390be2445afae8816d55340c380
Source dataset
uspto-grants-2009_05
Patent number
US07531666B2

Reaction notes

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