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

HRID 2247690
Notes
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Reaction equation

HRID 2247690 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:27][N:28]2[CH2:31][CH:30]([C:32]([O:34]C)=[O:33])[CH2:29]2)[S:6][C:7]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])=[CH:15][CH:14]=2)[O:10][N:9]=1)[CH3:2].O.[OH-].[Li+].C(O)(=O)C.C(O)(=O)C(O)=O>>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:27][N:28]2[CH2:31][CH:30]([C:32]([OH:34])=[O:33])[CH2:29]2)[S:6][C:7]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])=[CH:15][CH:14]=2)[O:10][N:9]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 971Oxalic AcidHCID 168937Lithium hydroxide, monohydrateHCID 68525364Methyl 1-[(4-ethyl-5-{5-[4-(2-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methyl]azetidine-3-carboxylate

Product 1

HCID 119780501-[(4-Ethyl-5-{5-[4-(2-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methyl]azetidine-3-carboxylic acid
Yield 42.3%

Procedure

The title compound (77 mg) was synthesized in a yield of 39% as a white crystalline solid by conducting the reaction similar to that mentioned in Example 1 (1g) using methyl 1-[(4-ethyl-5-{5-[4-(2-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methyl]azetidine-3-carboxylate (0.19 g, 0.38 mmol) that was obtained in Example 10 (10g), lithium hydroxide monohydrate (36 mg, 0.85 mmol), acetic acid (46 μL, 0.85 mmol), and oxalic acid (17 mg, 0.19 mmol).

Workup

  1. customthe reaction similar to

Sources & evidence

ORD record
ord-6a71bc40e2be4b8db5476799a21475ed
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07687491B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes