Hydrochloric Acid → Pantoprazole

HRID 2245619Notes

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-:26].[Na+].[O-]Cl.[Na+].Cl>S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].O.C(#N)C>[CH3:22][O:21][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:12][S+:11]([O-:26])[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

Conditions

Temperature: 5 °C

Procedure

A 1 L flat bottom flask equipped with a stirrer is charged with acetonitrile (0.6 L). Under mixing compound VI (200 g) is added, followed by water (0.2 L), and NaOH pellets (88 g, 4.0 eq.). The flask is cooled to 5° C. Aqueous 9.4% active NaOCl (540 g, d=1.16, 1.25 eq.) is added dropwise over 40 min. The two-phase mixture is then stirred at room temperature for 40 min at 10° C. Solid Na2S2O5 (6.6 g) is then added, and the mixture is stirred for another 0.5 h. The work up is finished by adjusting the pH to 8.5 with 32% HCl. A precipitate forms in the reaction mixture and is separated by filtration, washed with water, and dried to obtain pantoprazole (137.8 g, yield 66%) containing 0.02% sulfone and 0.01% compound VI within the limit of UV detection.

Workup

customA 1 L flat bottom flask equipped with a stirrer
stirringthe mixture is stirred for another 0.5 h
customA precipitate forms in the reaction mixture and is separated by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-fef6157b1ac64876a983c400dcdeca8c
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683177B2

Reaction notes

Loading…