Sodium Hydroxide → Pantoprazole sodium (USP)

HRID 585774Notes

Reaction equation

HRID 585774 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]>C(#N)C>[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 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

Pantoprazole free base (25 grams) was dissolved in a solution of acetonitrile (175 ml) and aqueous sodium hydroxide solution (2.7 grams in 5 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 acetonitrile (25 ml). Isopropyl ether (225 ml) was added slowly to the filtrate over a period of about ½ hour and the filtrate was stirred for about 1-2 hours to crystallize the solid mass. The separated solid mass was cooled to a temperature of 5-10° C. and further stirred for 3-4 hours. The solid was filtered, washed with Isopropyl ether (25 ml) and suck dried under vacuum. The wet solid was 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 acetonitrile (25 ml)
  4. additionIsopropyl ether (225 ml) was added slowly to the filtrate over a period of about ½ hour
  5. stirringthe filtrate was stirred for about 1-2 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 3-4 hours
  9. filtrationThe solid was filtered
  10. washwashed with Isopropyl ether (25 ml)
  11. customsuck dried under vacuum
  12. customThe wet solid was further dried at a temperature of 40-50° C.

Sources & evidence

ORD record
ord-5e41b3595c5a4214abd98b4ed4cf62a3
Source dataset
uspto-grants-2005_08
Patent number
US06933389B2

Reaction notes

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