Methanol → 3-Carboxymethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole
Reaction equation
[C:1]([CH2:3][C:4]1[N:8]=[C:7]([CH:9]([CH3:23])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([F:22])[CH:11]=2)[O:6][N:5]=1)#N.[OH-:24].[K+].C[OH:27]>O>[C:1]([CH2:3][C:4]1[N:8]=[C:7]([CH:9]([CH3:23])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([F:22])[CH:11]=2)[O:6][N:5]=1)([OH:27])=[O:24]Participants
5
Procedure
To a solution of 1.4 g of 3-cyanomethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole obtained in Example 38 in 50 ml of methanol was added a solution of 2.56 g of potassium hydroxide in 23 g of water. After stirring under reflux for 4 hours, the reaction mixture was cooled, diluted with water and extracted with chloroform. The organic phase was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed over silica gel using chloroformmethanol (20:1, v/v) to give 1.35 g of 3-carboxymethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole as an oil. It was crystallized from diisopropyl ether to give colorless fine needles, m.p. 100.5°-101.5° C.
Workup
- temperatureunder reflux for 4 hours
- temperaturethe reaction mixture was cooled
- extractionextracted with chloroform
- washThe organic phase was washed with water
- dry with materialdried over sodium sulfate
- customevaporated
- customThe residue was chromatographed over silica gel using chloroformmethanol (20:1
Sources & evidence
- ORD record
- ord-db7455bdb2cf4748826b194a4ae5ae2a
- Source dataset
- uspto-grants-1986_10
- Patent number
- US04618617
Reaction notes
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