Reaction equation
[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH3:10])[C:5]([CH2:11][S:12][C:13]2[NH:17][C:16]3[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=3[N:14]=2)=[N:4][CH:3]=1.CO.O.C1C=C(C([O-])=[O:34])C(C(O[O-])=O)=CC=1.[Mg+2].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[N:4][C:5]([CH2:11][S+:12]([O-:34])[C:13]2[NH:14][C:15]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:16]=3[N:17]=2)=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9]Participants
Conditions
- Temperature
- -10 °C
Procedure
To a solution of 3.44 g of pyrmetazole (10.5 mmol) in 30 mL of 9:1 v/v methanol/water at -10° C. was added dropwise a solution of 3.10 g of MMPP in 30 mL of 9:1 v/v methanol/water over a 10 minute period. The reaction mixture was stirred at -10° C. for 35 minutes then poured into a mixture of 100 mL of saturated aqueous sodium bicarbonate and 40 mL of methylene chloride. The layers were separated and the aqueous layer was extracted 3 times with methylene chloride. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under vacuum and the residue was slurried in EtOAc and the slurry stirred for 10 minutes. The solid was collected and then dried to provide 3.31 g of omeprazole (92% yield). LC analysis showed that the product was 99.5% pure.
Workup
- customThe layers were separated
- extractionthe aqueous layer was extracted 3 times with methylene chloride
- dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under vacuum
- stirringthe slurry stirred for 10 minutes
- customThe solid was collected
- customdried
Sources & evidence
- ORD record
- ord-22f30f4e398e46bb82be0430fa6320ff
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05391752
Linked notes
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