Hydrochloric Acid → HCID 136395593, compound

HRID 2378048Notes

Reaction equation

HRID 2378048 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:18]([C:27]3([C:30]([O:32][CH3:33])=[O:31])[CH2:29][CH2:28]3)(O)[O:17][N:16]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH3:33][O:32][C:30]([C:27]1([C:18]2[O:17][N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:28][CH2:29]1)=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68957797HCID 68957797, compound2×

Product 1

HCID 136395593HCID 136395593, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture consisting of 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropanecarboxylic acid methyl ester (Example 1, Compound C, 7.16 g) in dioxane (120 mL) is added concentrated aqueous hydrochloric acid (30 mL.) The mixture is brought to 100° C. for three hours. The mixture is cooled and is poured into ice water. The mixture is treated with sodium bicarbonate and is extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate and is filtered and concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography. Elution with hexanes-ethyl acetate (9:1 v/v) afforded the solid synthetic intermediate 1-[3-(4-hydroxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropanecarboxylic acid methyl ester (3.23 g, 9.63 mmol.)

Workup

  1. temperatureThe mixture is cooled
  2. extractionis extracted with ethyl acetate
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. filtrationis filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate is purified by flash silica gel column chromatography
  7. washElution with hexanes-ethyl acetate (9:1 v/v)

Sources & evidence

ORD record
ord-4c2137e2f2754e9fb83b4d637ca51f7c
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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