m-Chloroperbenzoic acid → HCID 178488147, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[NH:7][C:8]([S:10][CH2:11][C:12]3[C:17]([CH3:18])=[C:16]([O:19][CH3:20])[C:15]([CH3:21])=[CH:14][N:13]=3)=[N:9][C:5]=2[CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:29]>>[CH3:21][C:15]1[CH:14]=[N:13][C:12]([CH2:11][S+:10]([O-:29])[C:8]2[NH:7][C:6]3[CH:22]=[CH:23][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:9]=2)=[C:17]([CH3:18])[C:16]=1[O:19][CH3:20]Participants
3
Procedure
125 g of omeprazole, obtained by oxidation with 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1H-benzimidazole with 3-chloroperoxybenzoic acid, were dissolved while stirring in a mixture of 62.5 ml of 40% of methylamine and 125 ml of dichloromethane at room temperature. To this clear solution was added 2000 ml of acetone, the combined solution was stirred for 1 hour at room temperature and thereafter cooled to a temperature in the range of −10 to −15° C. The product formed was filtered off, washed with acetone and dried in vacuo at room temperature to constant weight. Yield: 103.7 g (83%).
Sources & evidence
- ORD record
- ord-5193851c75d242cd8424f2331f51ac31
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07553856B2
Reaction notes
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