Lansoprazole sulfide → Pantoprazole

HRID 2213877Notes

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.CC1C([O:44]CC(F)(F)F)=CC=NC=1CSC1NC2C=CC=CC=2N=1>>[CH3:22][O:21][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:12][S+:11]([O-:44])[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

Reactant 2

HCID 1094080Lansoprazole sulfide

HCID 9799341Pantoprazole sulfide

Product 1

HCID 178493214PantoprazoleYield 78%

Procedure

The experiment described in example 2 was repeated using 52.2 g 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl]methyl]thio]-1H-benzimidazole as substrate instead of Lansoprazole sulfide. 42.3 g of crystallized Pantoprazole are isolated after crystallization and drying (yield 78%).

Sources & evidence

ORD record: ord-53b123dc86d9478d986f24aef43d4ee9
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105681B2

Reaction notes

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