HCID 67457217, compound → 1-(4-(5-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid

HRID 1804452Notes

Reaction equation

HRID 1804452 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:34]=[CH:33][C:20]([CH2:21][N:22]5[CH2:25][CH:24]([C:26]([O:28]C(C)(C)C)=[O:27])[CH2:23]5)=[CH:19][CH:18]=4)[N:13]=3)[C:8]=2[C:35]([F:38])([F:37])[F:36])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>FC(F)(F)C(O)=O>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:34]=[CH:33][C:20]([CH2:21][N:22]5[CH2:25][CH:24]([C:26]([OH:28])=[O:27])[CH2:23]5)=[CH:19][CH:18]=4)[N:13]=3)[C:8]=2[C:35]([F:36])([F:37])[F:38])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 67457217HCID 67457217, compound

Product 1

HCID 468468201-(4-(5-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acidYield 74.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 1-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate (293 mg, 0.556 mmol) in trifluoroacetic acid (4 mL) was allowed to stand at room temperature for 1.5 h. The volatiles were removed under reduced pressure, and the residue was suspended in water (5 ml). The pH was adjusted to −4 with a 1N aqueous solution of sodium hydroxide with stirring. The resulting thick suspension was stirred at room temperature for 1 hr. The precipitate was collected by vacuum filtration and dried well under reduced pressure. The compound was suspended in methanol and stirred at room temperature for 18 hr. The product was collected by vacuum filtration, washed with methanol, and dried well under reduced pressure to afford 1-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid (194 mg, 0.412 mmol, 74.1% yield) as a white, crystalline solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. stirringThe resulting thick suspension was stirred at room temperature for 1 hr
  3. filtrationThe precipitate was collected by vacuum filtration
  4. customdried well under reduced pressure
  5. stirringstirred at room temperature for 18 hr
  6. filtrationThe product was collected by vacuum filtration
  7. washwashed with methanol
  8. customdried well under reduced pressure

Sources & evidence

ORD record
ord-059ab1a68eee4cee9e69a54411d61348
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

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