Hydrochloric Acid → 5-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid

HRID 1962992Notes

Reaction equation

HRID 1962992 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:16][O:17][C:18]=2[CH2:19][OH:20])=[CH:8][N:7]=1)=[O:5])C.O.[OH-].[Li+].Cl>C1COCC1.O.CO>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:15]2[C:14]([CH2:13][O:12][C:9]3[CH:10]=[CH:11][C:6]([C:4]([OH:5])=[O:3])=[N:7][CH:8]=3)=[C:18]([CH2:19][OH:20])[O:17][N:16]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 666445155-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 666443945-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acidYield 12.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester (5.8 g, 15.6 mmol) in THF (39 mL) was added a solution of lithium hydroxide monohydrate (762 mg, 31.2 mmol) in water (36 mL) and MeOH (10 mL) and the resulting mixture stirred at room temperature for 2 h. The mixture was acidified with HCl (1 N, 30 mL) and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated to afford the title compound (660 mg, 12%) which was obtained as a white solid. MS: m/e=343.0 [M−H]−.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0f0c953ed8e9472c838fccd9aec1021a
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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