Acetic Acid → HCID 67455256, compound

HRID 1804473Notes

Reaction equation

HRID 1804473 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([O:14]C)=[O:13])[C:8]=2[CH2:16][CH2:17][C:18]([F:21])([F:20])[F:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C(O)(=O)C>CO>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[C:8]=2[CH2:16][CH2:17][C:18]([F:20])([F:21])[F:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 67454167Methyl 5-phenyl-4-(3,3,3-trifluoropropyl)isoxazole-3-carboxylate

Product 1

HCID 67455256HCID 67455256, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 5-phenyl-4-(3,3,3-trifluoropropyl)isoxazole-3-carboxylate (25 mg, 0.084 mmol) and 1N aqueous sodium hydroxide (125 μL, 0.125 mmol) in methanol (1 mL) was heated at 23° C. for 2 h. To the reaction mixture was added acetic acid until the pH was ˜5. The mixture was purified by preparative HPLC to afford 5-phenyl-4-(3,3,3-trifluoropropyl)isoxazole-3-carboxylic acid (5 mg). The compound had an HPLC ret. time=3.16 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% MeOH−10% water−0.2% H3PO4; Start % B=0; Final % B=100. LC-MS: M+1=286+.

Workup

  1. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-db32757a959b4465869be75c0e7dc0ac
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

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