Hydrochloric Acid → Ethyl (2S)-2-(2,3,4-trifluoroanilino)propionate

HRID 458178

反応式

HRID 458178 の反応式
[F:1][C:2]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:3]=1[NH:4][C@@H:5]([CH3:9])[C:6]([OH:8])=[O:7].Cl.[CH2:17](O)[CH3:18]>>[F:1][C:2]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:3]=1[NH:4][C@@H:5]([CH3:9])[C:6]([O:8][CH2:17][CH3:18])=[O:7]

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 67366567(2S)-2-(2,3,4-trifluoroanilino)propionic acid

生成物 1

HCID 67368165Ethyl (2S)-2-(2,3,4-trifluoroanilino)propionate

実験手順

(2S)-2-(2,3,4-trifluoroanilino)propionic acid (219 mg; 99% ee) was dissolved in ethanol (2 ml) and hydrochloric acid (5 mol/l; 0.2 ml) was added thereto at room temperature. The liquid reaction mixture was heated under reflux for 6 hours and then the solvent was evaporated. To the obtained residue was added chloroform. Next, the organic layer was washed with a saturated aqueous solution of sodium chloride and water and dried over anhydrous magnesium sulfate. After evaporating the solvent, the obtained residue was subjected to silica gel column chromatography (ethyl acetate-normal hexane=1:4) to give the title compound (246 mg) as a pale yellow oily substance. The optical purity of the product was 99% ee. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 7.

後処理

  1. customat room temperature
  2. customThe liquid reaction mixture
  3. temperaturewas heated
  4. temperatureunder reflux for 6 hours
  5. customthe solvent was evaporated
  6. additionTo the obtained residue was added chloroform
  7. washNext, the organic layer was washed with a saturated aqueous solution of sodium chloride and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter evaporating the solvent

出典と根拠

ORDレコード
ord-fd838c83821a472aa22ebb8a525d65f8
出典データセット
uspto-grants-2007_03
特許番号
US07189847B2

関連ノート

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