Acetic Acid → 1-({5-[5-(3-Fluoro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-4-methyl-2-thienyl}methyl)azetidine-3-carboxylic acid

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[S:24][C:23]([CH2:25][N:26]4[CH2:29][CH:28]([C:30]([O:32]C)=[O:31])[CH2:27]4)=[CH:22][C:21]=3[CH3:34])[N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.[OH-].[Li+].C(O)(=O)C>>[F:1][C:2]1[CH:3]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[S:24][C:23]([CH2:25][N:26]4[CH2:27][CH:28]([C:30]([OH:32])=[O:31])[CH2:29]4)=[CH:22][C:21]=3[CH3:34])[N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 168937Lithium hydroxide, monohydrate

HCID 68525875Methyl 1-({5-[5-(3-fluoro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-4-methyl-2-thienyl}methyl)azetidine-3-carboxylate

Product 1

HCID 119779371-({5-[5-(3-Fluoro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-4-methyl-2-thienyl}methyl)azetidine-3-carboxylic acidYield 76.1%

Procedure

The title compound (0.17 g) was synthesized in a yield of 74% as a white crystalline solid by conducting the reaction similar to that mentioned in Example 2 (2e) using methyl 1-({5-[5-(3-fluoro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-4-methyl-2-thienyl}methyl)azetidine-3-carboxylate (0.23 g, 0.48 mmol) that was obtained in Example 11 (11g), lithium hydroxide monohydrate (46 mg, 1.1 mmol), and acetic acid (60 μL, 1.1 mmol).