Hydrochloric Acid → Pantoprazole

HRID 2245618Notes

Reaction equation

HRID 2245618 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>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

7

Reactant 5

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

Product 1

HCID 178493214PantoprazoleYield 64.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-7 °C

Procedure

A flask equipped with a stirrer is charged with acetonitrile (0.6 L). Under mixing, compound VI (30 g) is added, followed by 18.8% aqueous NaOH (70 ml, 5.0 eq.). The flask is then cooled to −7° C. Aqueous 10.6% active NaOCl (70 ml, d=1.16, 1.4 eq.) is added dropwise over 45 min. The two-phase mixture is stirred at room temperature for 1.5 h. Aqueous Na2S2O5 (120 ml) is added. The pH is then adjusted to 8 with 10% HCl solution (120 ml). The phases are separated. The organic layer is washed with water, and the aqueous phase is washed twice with acetonitrile. The organic phases are combined, dried over MgSO4, and concentrated to one quarter of their original volume. Pantoprazole is precipitated from the concentrate and separated by filtration to yield pantoprazole (20.1 g, 64.8%) containing 0.04% compound VI and free of sulfone within the limit of UV detection.

Workup

  1. customA flask equipped with a stirrer
  2. additionUnder mixing
  3. customThe phases are separated
  4. washThe organic layer is washed with water
  5. washthe aqueous phase is washed twice with acetonitrile
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to one quarter of their original volume
  8. customPantoprazole is precipitated from the
  9. concentrationconcentrate
  10. customseparated by filtration

Sources & evidence

ORD record
ord-7361d8d3e56a4a3e860c4e01dadf50f6
Source dataset
uspto-grants-2010_03
Patent number
US07683177B2

Reaction notes

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