Hydrochloric Acid → Pantoprazole

HRID 2245620Notes

Reaction equation

HRID 2245620 reaction equation
[F:1][CH:2]([F:25])[O:3][C:4]1[CH:24]=[CH:23][C:7]2[NH:8][C:9]([S:11][CH2:12][C:13]3[C:18]([O:19][CH3:20])=[C:17]([O:21][CH3:22])[CH:16]=[CH:15][N:14]=3)=[N:10][C:6]=2[CH:5]=1.[OH-].[Na+].[O-]Cl.[Na+].S(S([O-])=O)([O-])(=O)=[O:32].[Na+].[Na+].Cl>O.C(#N)C>[CH3:22][O:21][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:12][S+:11]([O-:32])[C:9]2[NH:8][C:7]3[CH:23]=[CH:24][C:4]([O:3][CH:2]([F:1])[F:25])=[CH:5][C:6]=3[N:10]=2)[C:18]=1[O:19][CH3:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 656671Sodium PyrosulfiteHCID 9799341Pantoprazole sulfideHCID 23665760Sodium Hypochlorite2×

Product 1

HCID 178493214PantoprazoleYield 53.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
-7 °C

Procedure

A flask is charged with acetonitrile (0.1 L). Under mixing, compound VI (5 g) is added, followed by NaOH pellets (2.18 g, 4.0 eq.). The reactor is cooled to −7° C. A commercial 10.5% NaOCl solution (11.5 ml, 1.4 eq.) is diluted by a factor of 3 by adding water. The diluted NaOCl solution (34.5 ml) is added dropwise over 25 min. The two-phase mixture is stirred at room temperature for 2.5 h. Then, aqueous Na2S2O5 (20 ml) is added. The pH of the aqueous phase is adjusted to 8 with 10% HCl (10 ml). The phases are then separated. The organic layer is washed with water, and the aqueous phase is washed twice with acetonitrile. The combined organic phases are combined, dried over magnesium sulfate (MgSO4), and concentrated to one quarter of the original volume. A precipitate forms in the concentrate, which is separated by filtration to obtain pantoprazole (2.78 g, 53.8%) containing 0.07% compound VI and free of sulfone within the limited of UV detection.

Workup

  1. additionUnder mixing
  2. customThe phases are then separated
  3. washThe organic layer is washed with water
  4. washthe aqueous phase is washed twice with acetonitrile
  5. dry with materialdried over magnesium sulfate (MgSO4)
  6. concentrationconcentrated to one quarter of the original volume
  7. customA precipitate forms in the concentrate, which is separated by filtration

Sources & evidence

ORD record
ord-6902603fb39c4b9e959c0ac5af5552dc
Source dataset
uspto-grants-2010_03
Patent number
US07683177B2

Reaction notes

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