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

HRID 1616611Notes

Reaction equation

HRID 1616611 reaction equation
[Li+].[OH-:2].CO[C:5](=O)[CH2:6][CH2:7][CH2:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20]C)[O:11][N:10]=1.Cl.[O:24]1[CH2:29]COCC1>O>[OH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12]1[O:11][N:10]=[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][C:29]([OH:24])=[O:2])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 591677844-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-butyric acid methyl ester

Product 1

HCID 1364006025-[5-(2-Hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add a solution of LiOH (1.04 g, 43.6 mmol) in water (15 mL) to a rapidly stirred solution of 4-[5-(2-methoxy-phenyl)-isoxazol-3-yl]-butyric acid methyl ester (2.28 g, 8.7 mmol) in dioxane (120 mL), stir at room temperature overnight After 1 hour, acidify to pH 1 with 5N HCl solution and concentrate to remove the majority of the dioxane. Add water to residue and place in refrigerator overnight Filter out solids, wash with water, dry in a 50° C. vacuum oven for 6 hours to afford the title compound (3.11 g, 87%). MS (IS) 262 (M+1)+.

Workup

  1. concentrationconcentrate
  2. customto remove the majority of the dioxane
  3. customplace in refrigerator overnight
  4. filtrationFilter out solids
  5. washwash with water
  6. customdry in a 50° C. vacuum oven for 6 hours

Sources & evidence

ORD record
ord-f5e5a77ccbfa4392aa6f9909b7cbbf3e
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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