Sodium Hydroxide → Lansoprazole

HRID 1444742Notes

Reaction equation

HRID 1444742 reaction equation
O.[CH3:2][C:3]1[C:4]([CH2:15][S:16][C:17]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=2)=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([F:14])([F:13])[F:12].C(N)(N)=[O:27].OO.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>C(O)C.O>[CH3:2][C:3]1[C:4]([CH2:15][S:16]([C:17]2[NH:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)=[O:27])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([F:13])([F:12])[F:14]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 31294Carbamide PeroxideHCID 61475Sodium Thiosulfate PentahydrateHCID 195984462-(((3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole hydrate

Product 1

HCID 3883LansoprazoleYield 120.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Conditions

Temperature
11 °C

Procedure

40 g (0.1077 mole) 2-[[[3-methyl-4-(2,2,2-trifluoro-ethoxy)-2-pyridinyl]methyl]thio]-1H-benzimidazole hydrate was suspended in 240 ml of ethanol and 0.264 g (1.077 mmole) vanadium(V) oxytriisopropoxide dissolved in 1 ml of ethanol were added at room temperature (20-25° C.). The suspension was cooled to 10-12° C. and 12.14 g (0.129 mole) hydrogen peroxide urea adduct were added. The reaction was carried out at 10-15° C. for two hours and then at 5-10° C. until the reaction was completed. At the end of the reaction (3-6 hours, depending upon the temperature), 6 g of sodium thiosulphate pentahydrate in a solution of 40 ml water and 120 ml ethanol were added at 5-10° C., the mixture was stirred for one hour at 10-15° C. and 0.5 ml of 30% aqueous solution of sodium hydroxide were added to achieve a pH of about 10. The suspension was heated to 50-55° C., hot filtered and then gradually cooled to room temperature in one hour and then to 5-10° C. in half to one hour and agitated at that temperature for another one hour. The product was filtered off to obtain 48 g of wet lansoprazole.

Workup

  1. additionwere added at room temperature (20-25° C.)
  2. customat 5-10° C.
  3. customAt the end of the reaction (3-6 hours
  4. additionwere added at 5-10° C.
  5. temperatureThe suspension was heated to 50-55° C.
  6. filtrationhot filtered
  7. temperaturegradually cooled to room temperature in one hour
  8. waitto 5-10° C. in half to one hour
  9. stirringagitated at that temperature for another one hour
  10. filtrationThe product was filtered off

Sources & evidence

ORD record
ord-54388d676a494bbe89c7bdc74925b54a
Source dataset
uspto-grants-2010_02
Patent number
US07662968B2

Reaction notes

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