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

HRID 8451

반응식

HRID 8451 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0fb84b9cd02047b8b821ce5357076070
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087778B2

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