Sodium Hydroxide → Pantoprazole sodium (USP)

HRID 585775Notes

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([O:33]C)(C)(C)C>C(OCC)(=O)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].[OH2:33].[OH2:27].[OH2:2].[Na+:28].[Na+:28]

Participants

Conditions

Temperature: 45 °C

Procedure

Pantoprazole freebase (25 grams) was dissolved in a solution of ethyl acetate (50 ml) and aqueous sodium hydroxide solution (2.7 grams in 5 ml of water) and stirred at a temperature of 40-50° C. till the clear solution results. Methyl tertiary butyl ether (250 ml) was added to the reaction mixture and stirred for about 3-4 hours to crystallize the solid mass. The separated solid mass was filtered, washed with methyl tertiary butyl ether (50 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

customresults
stirringstirred for about 3-4 hours
customto crystallize the solid mass
filtrationThe separated solid mass was filtered
washwashed with methyl tertiary butyl ether (50 ml)
customsuck dried under vacuum
customThe wet solid was further dried at a temperature of 40-50° C.

Sources & evidence

ORD record: ord-43bdbdff25ab423cacdd26ba42ac6d59
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933389B2

Reaction notes

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