Acetic Acid → 4-Cyclopropyl-5-phenylisoxazole-3-carboxylic acid

HRID 1804466Notes

Reaction equation

HRID 1804466 reaction equation
[CH:1]1([C:4]2[C:5]([C:15]([O:17]C)=[O:16])=[N:6][O:7][C:8]=2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3][CH2:2]1.[OH-].[Na+].C(O)(=O)C>CO>[CH:1]1([C:4]2[C:5]([C:15]([OH:17])=[O:16])=[N:6][O:7][C:8]=2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 58537215Methyl 4-cyclopropyl-5-phenylisoxazole-3-carboxylate

Product 1

HCID 585372244-Cyclopropyl-5-phenylisoxazole-3-carboxylic acidYield 77.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-cyclopropyl-5-phenylisoxazole-3-carboxylate (170 mg, 0.699 mmol) and 1N aqueous sodium hydroxide (1 mL, 1.05 mmol) in methanol (6 mL) was heated to 80° C. in a sealed tube for 1 hr. The reaction mixture was acidified with acetic acid until the pH was ˜4. The mixture was concentrated, and the residue was purified by preparative HPLC to give 4-cyclopropyl-5-phenylisoxazole-3-carboxylic acid (124 mg). The compound had an HPLC ret. time=2.81 min.−Column. YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO4; Solvent B=90%

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-11f6acead73d4c209878d8a5397e429b
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

Loading…