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

HRID 2247698Notes

Reaction equation

HRID 2247698 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

4

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 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).

Workup

  1. customthe reaction similar to

Sources & evidence

ORD record
ord-c6979f58367147768161fc02e1e6a94b
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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