Isobutyl Acetate → Pantoprazole

HRID 2245621Notes

Reaction equation

HRID 2245621 reaction equation
C(OCC(C)C)(=[O:3])C.[F:9][CH:10]([F:33])[O:11][C:12]1[CH:32]=[CH:31][C:15]2[NH:16][C:17]([S:19][CH2:20][C:21]3[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=[CH:23][N:22]=3)=[N:18][C:14]=2[CH:13]=1.[OH-].[Na+].[O-]Cl.[Na+]>S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[CH3:30][O:29][C:25]1[CH:24]=[CH:23][N:22]=[C:21]([CH2:20][S+:19]([O-:3])[C:17]2[NH:16][C:15]3[CH:31]=[CH:32][C:12]([O:11][CH:10]([F:9])[F:33])=[CH:13][C:14]=3[N:18]=2)[C:26]=1[O:27][CH3:28]

Participants

6

Reactant 4

HCID 8038Isobutyl AcetateHCID 14798Sodium HydroxideHCID 9799341Pantoprazole sulfideHCID 23665760Sodium Hypochlorite

Product 1

HCID 178493214PantoprazoleYield 83%

Reagents, catalysts & solvents 1

HCID 656671Sodium PyrosulfiteSolvent

Conditions

Temperature
-7 °C

Procedure

A flask is charged with isobutyl acetate (0.1 L). Under mixing, compound VI (5 g) is added, followed by 18.8% NaOH (11.5 ml, 4.9 eq.). The flask is cooled to −7° C. Then, aqueous 9.4% active NaOCl (11.5 ml, 1.24 eq.) is added dropwise over 15 min. The two-phase mixture is stirred at room temperature overnight, over which time a precipitate forms. Aqueous Na2S2O5 (20 ml) is then added and the precipitate is redissolved. On standing, another precipitate forms in the mixture which is separated by filtration and dried to give pantoprazole (4.33 g, 83%) containing 0.4% compound VI and free of sulfone within the limit of UV detection.

Workup

  1. additionUnder mixing
  2. dissolutionthe precipitate is redissolved
  3. customanother precipitate forms in the mixture which is separated by filtration
  4. customdried

Sources & evidence

ORD record
ord-e02c7179def843cdabc19475f34a2508
Source dataset
uspto-grants-2010_03
Patent number
US07683177B2

Reaction notes

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