Triphenylphosphine → Lansoprazole sulfide
Reaction equation
O[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][N:4]=1.[SH:16][C:17]1[NH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:9][C:8]1[C:3]([CH2:2][S:16][C:17]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:10][CH2:11][C:12]([F:15])([F:14])[F:13]Participants
Procedure
A mixture of 6.63 g of 2-hydroxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine(30 mmol), 4.5 g of 2-mercaptobenzimidazol(30 mmol) and 8.67 g of triphenyl phosphine(33 mmol) was dissolved in 100 ml of tetrahydrofuran, 5.75 g of diethyl azodicarboxylate(DEAD)(33 mmol) dissolved in 30 ml of tetrahydrofuran was added dropwise thereto at room temperature, and stirred for 1 hour. The reaction mixture was concentrated under a reduced pressure, the resulting residue was combined with looml of ethylacetate, and extracted twice with 50 ml portions of 1N—HCl. The aqueous layer was then washed with 50 ml of diethylether; neutralized with 1N—NaOH to adjust the pH to 7. The resulting precipitates were filtrated, washed with water, and dried, to obtain 10.06 g of the title compound as a white solid(yield: 95%).
Workup
- additionwas added dropwise
- concentrationThe reaction mixture was concentrated under a reduced pressure
- extractionextracted twice with 50 ml portions of 1N—HCl
- washThe aqueous layer was then washed with 50 ml of diethylether
- customThe resulting precipitates
- filtrationwere filtrated
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-e3319f3cbbfd444cb747f202c54c6f30
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06423846B1
Reaction notes
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