Hydrogen Peroxide → Lansoprazole

HRID 2213874Notes

Reaction equation

HRID 2213874 reaction equation
[CH3:1][C:2]1[C:3]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:4][CH:5]=[N:6][C:7]=1[CH2:8][S:9][C:10]1[NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[N:18]=1.C[OH:26].OO>C[Re](=O)(=O)=O.O>[CH3:1][C:2]1[C:7]([CH2:8][S:9]([C:10]2[NH:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[N:18]=2)=[O:26])=[N:6][CH:5]=[CH:4][C:3]=1[O:19][CH2:20][C:21]([F:24])([F:22])[F:23]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 1094080Lansoprazole sulfide

Product 1

HCID 3883Lansoprazole

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

In a 1-liter flask equipped with dropping funnel and mechanical stirring 50 g (0.142 moles) of Lansoprazole sulfide, 35.0 mg (0.00014 moles) of methyltrioxorhenium (Aldrich) and 500 ml of methanol are charged. The temperature of the solution is brought to 5° C., and then 17.8 g (0.173 moles) of a 33% (v/v) aqueous solution of hydrogen peroxide are added. The mixture is maintained at 5° C. for 4 hours, then 1000 ml of cold deionized water are added, whereby a dense precipitate forms. The mixture is stirred for 1 additional hour at 5° C. and is then filtered on a Buchner, the cake is washed with 3×100 ml of cold deionized water and is discharged. The wet solid weighs 59.5 g. A 1 g sample is collected and dried under vacuum (50 mmHg) at 40° C. for 12 hours, which loses 16.5% of its weight. The yield of crude product is thus 95%. The amount of residual water in the crystalline solid is calculated through the Karl-Fischer method and the solid is then recrystallised, talking into account the amount of residual water, from 8 volumes of a 9:1 mixture of ethanol and water. The yield of the crystallized, dried product starting from the sulfide is 75%, the purity of the product is >99.5% (HPLC).

Workup

  1. customIn a 1-liter flask equipped
  2. additionare charged
  3. customis brought to 5° C.
  4. additionare added
  5. filtrationis then filtered on a Buchner
  6. washthe cake is washed with 3×100 ml
  7. customA 1 g sample is collected
  8. customdried under vacuum (50 mmHg) at 40° C. for 12 hours
  9. customthe solid is then recrystallised
  10. additionfrom 8 volumes of a 9:1 mixture of ethanol and water

Sources & evidence

ORD record
ord-ceca254de10e4761aea6f49137b5bc48
Source dataset
uspto-grants-2006_09
Patent number
US07105681B2

Reaction notes

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