Methanol → HCID 20230226, compound

Reaction equation

[C:1]([CH2:4][C:5]1[N:9]=[C:8]([CH:10]([CH3:24])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([F:23])[CH:12]=2)[O:7][N:6]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH3:30]O>>[CH3:30][O:2][C:1]([CH2:4][C:5]1[N:9]=[C:8]([CH:10]([CH3:24])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([F:23])[CH:12]=2)[O:7][N:6]=1)=[O:3]

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 136909693-Carboxymethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

Product 1

HCID 20230226HCID 20230226, compound

Procedure

To a solution of 1.27 g of 3-carboxymethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole obtained in Example 39 in 20 ml of dry methanol was added a drop of conc. sulfuric acid. The mixture was allowed to stand at room temperature overnight and then concentrated to dryness under reduced pressure. The solution of the residue in benzene was washed successively with a sodium bicarbonate solution and water, dried over sodium sulfate and evaporated. The residue was chromatographed over silica gel using benzene to give 0.95 g of 3-methoxycarbonylmethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole, nD25 1.5618.