Hydrochloric Acid → Methyl2-(2,3,4-trifluoroanilino)propionate

HRID 8451

反応式

HRID 8451 の反応式
[F:1][C:2]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:3]=1[NH:4][C@H:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7].N12CCCN=C1CCCCC2.Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:3]=1[NH:4][CH:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10149157Methyl (2R)-2-(2,3,4-trifluoroanilino)propionate

生成物 1

HCID 22015876Methyl2-(2,3,4-trifluoroanilino)propionate収率 86.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

Methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (100 mg, 38% ee) was dissolved in toluene (2 ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 71.8 mg) was added thereto at room temperature. Then the liquid reaction mixture was stirred at 110° C. for 16 hours. After adding hydrochloric acid (1 mol/l; 1 ml) to the liquid reaction mixture, the aqueous layer was extracted with toluene. The organic layer was washed with water and a saturated aqueous solution of sodium chloride 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 thereby give the title compound (86.8 mg) as colorless crystals. The optical purity of this product was 0% ee. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 5.

後処理

  1. customat room temperature
  2. customThen the liquid reaction mixture
  3. customto the liquid reaction mixture
  4. extractionthe aqueous layer was extracted with toluene
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  7. customAfter evaporating the solvent

出典と根拠

ORDレコード
ord-0fb84b9cd02047b8b821ce5357076070
出典データセット
uspto-grants-2006_08
特許番号
US07087778B2

関連ノート

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