Hydrochloric Acid → 5-[5-(5-Chloro-2-hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acid

HRID 1616601Notes

Reaction equation

HRID 1616601 reaction equation
O[Li].O.C([O:6][C:7](=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[OH:24])[O:14][N:13]=1)C.Cl>O.O1CCOCC1>[Cl:23][C:21]1[CH:20]=[CH:19][C:18]([OH:24])=[C:17]([C:15]2[O:14][N:13]=[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][C:7]([OH:25])=[O:6])[CH:16]=2)[CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 1364006035-[5-(5-Chloro-2-hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester

Product 1

HCID 1362065305-[5-(5-Chloro-2-hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acidYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Add a solution of LiOH.H2O (2.14 g, 51.0 mmol) in water (30 mL) to a rapidly stirred solution of 5-[5-(5-chloro-2-hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester (3.30 g, 10.2 mmol) in dioxane (60 mL), stir at room temperature overnight. After 1 hour, acidify to pH 1 with 5N HCl solution and place in refrigerator. Filter out solids and rinse with water to afford the title compound (2.73 g, 91%). MS (IS) 296 (M+1)+.

Workup

  1. waitAfter 1 hour
  2. filtrationFilter out solids
  3. washrinse with water

Sources & evidence

ORD record
ord-d8e57f9f68f8493fb0b4bdfcbb23dd60
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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