Acetic Acid → 1-[(5-{5-[3-Chloro-4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-4-ethyl-2-thienyl)methyl]azetidine-3-carboxylic acid

HRID 2247714Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:16]2[O:20][N:19]=[C:18]([C:21]3[S:25][C:24]([CH2:26][N:27]4[CH2:30][CH:29]([C:31]([O:33]C)=[O:32])[CH2:28]4)=[CH:23][C:22]=3[CH2:35][CH3:36])[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1.[OH-].[Na+].C(O)(=O)C>>[Cl:1][C:2]1[CH:3]=[C:4]([C:16]2[O:20][N:19]=[C:18]([C:21]3[S:25][C:24]([CH2:26][N:27]4[CH2:30][CH:29]([C:31]([OH:33])=[O:32])[CH2:28]4)=[CH:23][C:22]=3[CH2:35][CH3:36])[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 14798Sodium Hydroxide

HCID 68523766Methyl 1-[(5-{5-[3-chloro-4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-4-ethyl-2-thienyl)methyl]azetidine-3-carboxylate

Product 1

HCID 119780491-[(5-{5-[3-Chloro-4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-4-ethyl-2-thienyl)methyl]azetidine-3-carboxylic acidYield 92%

Procedure

The title compound (0.14 g) was synthesized in a yield of 92% as a white crystalline solid by conducting the reaction similar to that mentioned in Example 3 (3e) using methyl 1-[(5-{5-[3-chloro-4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-4-ethyl-2-thienyl)methyl]azetidine-3-carboxylate (0.16 g, 0.30 mmol) that was obtained in Example 16 (16c), a 1 N aqueous solution of sodium hydroxide (0.89 mL, 0.89 mmol), and acetic acid (51 μL, 0.89 mmol).

Workup

customthe reaction similar to

Sources & evidence

ORD record: ord-42a9cb5f22c242c39ffd9069a46f0df9
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687491B2

Reaction notes

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