Hydrochloric Acid → HCID 136395593, 화합물

HRID 2378048노트

반응식

HRID 2378048 반응식
[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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68957797HCID 68957797, 화합물2회

생성물 1

HCID 136395593HCID 136395593, 화합물수율 62.9%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.)

후처리

  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)

출처 및 근거

ORD 기록
ord-4c2137e2f2754e9fb83b4d637ca51f7c
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470715B2

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