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

HRID 2247648Notes

Reaction equation

HRID 2247648 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]([CH2:26][N:27]5[CH2:30][CH:29]([C:31]([O:33]CC)=[O:32])[CH2:28]5)[S:24][CH:25]=4)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C(O)(=O)C.CO>O1CCOCC1.O>[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]([CH2:26][N:27]5[CH2:30][CH:29]([C:31]([OH:33])=[O:32])[CH2:28]5)[S:24][CH:25]=4)[N:17]=3)[S:10][C:11]=2[C:12]([F:14])([F:13])[F:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 68526579HCID 68526579, compound

Product 1

HCID 573984681-[(4-{5-[4-Phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methyl]azetidine-3-carboxylic acidYield 53.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 1-[(4-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methyl]azetidine-3-carboxylate (70 mg, 0.13 mmol) that was obtained in Example 3 (3d) in dioxane (2 ml) was added a 1N aqueous solution of sodium hydroxide (0.39 ml, 0.39 mmol) with stirring, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, acetic acid (22 μl, 0.39 mmol) was added to the reaction mixture to quench the reaction, and the resulting mixture was evaporated in vacuo. To the residue thus obtained were added successively methanol (1 ml) and water (1 ml) with stirring, and the white solid precipitated was collected by filtration using a Kiriyama funnel, washed with a mixed solvent of water and methanol (3:7) and dried in vacuo to afford the title compound (34 mg) in a yield of 53% as a crystalline white solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. stirringAfter stirring
  3. customto quench
  4. customthe reaction
  5. customthe resulting mixture was evaporated in vacuo
  6. customTo the residue thus obtained
  7. stirringwith stirring
  8. customthe white solid precipitated
  9. filtrationwas collected by filtration
  10. washwashed with a mixed solvent of water and methanol (3:7)
  11. customdried in vacuo

Sources & evidence

ORD record
ord-8c425b50a0084e9ba730d41ab1dc3814
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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