Hydrochloric Acid → HCID 90202470, compound

HRID 929755Notes

Reaction equation

HRID 929755 reaction equation
C([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)=[CH:13][CH:12]=2)[CH:7]=1)=[O:5])C.[OH-].[K+].Cl>C1COCC1>[F:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[O:10][N:9]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 90202458HCID 90202458, compound2×

Product 1

HCID 90202470HCID 90202470, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[4-(3-Fluoro-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid ethyl ester (which may be prepared as described in Preparation of Intermediate 4; 500 mg, 1.47 mmol) was dissolved in THF (5 mL), and 0.5 M aqueous KOH (12 mL, 1 mmol) was added. The reaction mixture was heated at reflux, cooled to room temperature, and then to 0° C. The mixture was acidified by the addition of 4 M aqueous HCl (10 mL). The resulting solid was filtered off and washed with cold H2O to give 3-[4-(3-fluoro-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid (431 mg, 94%). HRMS Calcd. for C17H13FNO4 (M+H)+, 314.0823. Found: 314.0823.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux
  3. customto 0° C
  4. filtrationThe resulting solid was filtered off
  5. washwashed with cold H2O

Sources & evidence

ORD record
ord-d7f1b42ffd4942318cdc8731d0cbea39
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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