Trifluoroacetic acid → 2-[(4-{2-[(4'-Fluorobiphenyl-4-yl)oxy]-1-hydroxyethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid

HRID 456022ノート

反応式

HRID 456022 の反応式
C([O:5][C:6](=[O:33])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH:16]([OH:32])[CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH:16]([C:14]3[N:15]=[C:11]([S:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:33])=[O:5])[S:12][CH:13]=3)[OH:32])=[CH:24][CH:23]=2)=[CH:26][CH:27]=1

参加物

6

反応物 2

HCID 6422Trifluoroacetic acidHCID 584514012-[(4-{2-[(4'-Fluorobiphenyl-4-yl)oxy]-1-hydroxyethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

生成物 1

HCID 462094152-[(4-{2-[(4'-Fluorobiphenyl-4-yl)oxy]-1-hydroxyethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid収率 58%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-[(4-{2-[(4′-Fluorobiphenyl-4-yl)oxy]-1-hydroxyethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (877 mg) obtained in Example 2-2 was dissolved in methylene chloride (3 mL), trifluoroacetic acid (3 mL) was added and the mixture was stirred at room temperature overnight. The solvent was evaporated and the obtained residue was dissolved in ethyl acetate (30 mL), washed successively with water and saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was applied to column chromatography (Moritex Corporation Purif Pack SI 60 μm size 200 was used. elution solvent: hexane/ethyl acetate=7/3→0/10). The solvent was evaporated from the obtained fraction containing the object product to give a white solid. This was dissolved in a mixed solvent of hexane and ethyl acetate with heating, and the mixture was cooled to allow precipitation of a solid to give the title compound (450.6 mg).

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe obtained residue was dissolved in ethyl acetate (30 mL)
  3. washwashed successively with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. washthe obtained residue was applied to column chromatography (Moritex Corporation Purif Pack SI 60 μm size 200 was used. elution solvent: hexane/ethyl acetate=7/3→0/10)
  7. customThe solvent was evaporated from the obtained fraction
  8. additioncontaining the object product
  9. customto give a white solid
  10. temperaturewith heating
  11. temperaturethe mixture was cooled
  12. customprecipitation of a solid

出典と根拠

ORDレコード
ord-33ab561cd88547abb0d6ba96737cf1df
出典データセット
uspto-grants-2013_07
特許番号
US08497382B2

反応ノート

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