Sodium Hydroxide → Pantoprazole sodium (USP)

HRID 585773Notes

Reaction equation

HRID 585773 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][N:6]=[C:7]([CH2:11][S+:12]([O-:26])[C:13]2[NH:14][C:15]3[CH:16]=[CH:17][C:18]([O:22][CH:23]([F:25])[F:24])=[CH:19][C:20]=3[N:21]=2)[C:8]=1[O:9][CH3:10].[OH-:27].[Na+:28]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][N:6]=[C:7]([CH2:11][S:12]([C:13]2[N-:14][C:15]3[CH:16]=[CH:17][C:18]([O:22][CH:23]([F:24])[F:25])=[CH:19][C:20]=3[N:21]=2)=[O:26])[C:8]=1[O:9][CH3:10].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][N:6]=[C:7]([CH2:11][S:12]([C:13]2[N-:14][C:15]3[CH:16]=[CH:17][C:18]([O:22][CH:23]([F:24])[F:25])=[CH:19][C:20]=3[N:21]=2)=[O:26])[C:8]=1[O:9][CH3:10].[OH2:27].[OH2:2].[OH2:2].[Na+:28].[Na+:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178493214Pantoprazole

Product 1

HCID 11954257Pantoprazole sodium (USP)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Pantoprazole free base (50 grams) was dissolved in a solution of tetrahydrofuran (350 ml) and aqueous sodium hydroxide solution (5.4 grams dissolved in 10 ml of water), and stirred at a temperature of 25-35° C. till the clear solution results. The reaction solution was filtered through hyflow and washed the bed with tetrahydrofuran (2×25 ml). Dichloromethane (400 ml) was added slowly to the filtrate over a period of about 1 hour and stirred for about 5-6 hours to crystallize the solid mass. The separated solid mass was cooled to a temperature of 5-10° C. and further stirred for about 2-3 hours. The solid was filtered, washed with dichloromethane (2×25 ml) and suck dried under vacuum. The wet solid was suspended in dichloromethane (250 ml) and stirred for about 15-30 minutes. Then the solid was filtered and suck dried under vacuum and further dried at a temperature of 40-50° C. to afford crystalline Form-I of Pantoprazole sodium sesquihydrate.

Workup

  1. customresults
  2. filtrationThe reaction solution was filtered through hyflow
  3. washwashed the bed with tetrahydrofuran (2×25 ml)
  4. additionDichloromethane (400 ml) was added slowly to the filtrate over a period of about 1 hour
  5. stirringstirred for about 5-6 hours
  6. customto crystallize the solid mass
  7. temperatureThe separated solid mass was cooled to a temperature of 5-10° C.
  8. stirringfurther stirred for about 2-3 hours
  9. filtrationThe solid was filtered
  10. washwashed with dichloromethane (2×25 ml)
  11. customsuck dried under vacuum
  12. stirringstirred for about 15-30 minutes
  13. filtrationThen the solid was filtered
  14. customsuck dried under vacuum
  15. customfurther dried at a temperature of 40-50° C.

Sources & evidence

ORD record
ord-9ea660c561f642d391a41a3fa2790c08
Source dataset
uspto-grants-2005_08
Patent number
US06933389B2

Reaction notes

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