Acetic Acid → Lansoprazole

HRID 394825

Reaction equation

HRID 394825 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].C([O-])([O-])=[O:26].C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+].O.C(O)(=O)C>CO.[NH4+].[NH4+].[O-][Mo]([O-])(=O)=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-:26])[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 4

HCID 176Acetic AcidHCID 962WaterHCID 159762Sodium percarbonateHCID 1094080Lansoprazole sulfide

Product 1

HCID 3883LansoprazoleYield 238.6%

Reagents, catalysts & solvents 2

HCID 61578Diammonium molybdateCatalystHCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

10 g of 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]thio]-1H-benzimidazol were dissolved in 50 ml of methanol and 0.3 g of ammonium molybdate were added. The solution was cooled to 10° C., and 3.35 g of sodium percarbonate added slowly, kept stirred at the same temperature for 15 hours. After the reaction ended 250 ml of water were added and the pH of the resulting mixture adjusted to 10 with 10% acetic acid. This was kept stirred for 1 hour and the solid obtained was filtered, and subsequently washed with water and dried in a vacuum oven at 40° C. This provided 9.4 g of lansoprazol (yield: 90%).

Workup

  1. additionwere added
  2. stirringThis was kept stirred for 1 hour
  3. customthe solid obtained
  4. filtrationwas filtered
  5. washsubsequently washed with water
  6. customdried in a vacuum oven at 40° C

Sources & evidence

ORD record
ord-858f083ce39e4c66a135dc371a8ec34e
Source dataset
uspto-grants-2003_08
Patent number
US06603009B2

Linked notes

Loading…