Water → Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate

HRID 8472

반응식

HRID 8472 반응식
[OH-].[K+].[F:3][C:4]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:5]=1[NH:6][C@@H:7]([CH3:10])[CH2:8][OH:9].[CH2:17]([O:19][C:20](=[O:31])[C:21](=[CH:27]OCC)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:18].O>[Cl-].C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC.CN(C=O)C>[F:3][C:4]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:5]=1[N:6]([CH:27]=[C:21]([C:20]([O:19][CH2:17][CH3:18])=[O:31])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C@@H:7]([CH3:10])[CH2:8][OH:9]

참가 물질

7

반응물 4

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 14797Potassium HydroxideHCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanol

생성물 1

HCID 11485652Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate수율 90.2%

시약·촉매·용매 2

HCID 80021Tetrahexylammonium chloride촉매HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

At room temperature, potassium hydroxide (330 mg) and tetrahexylammonium chloride (190.1 mg) were dissolved in DMF (15 ml). After adding a solution (5 ml) of (2S)-2-(2,3,4-trifluoroanilino)propanol (1 g, 99.8% ee) and diethylethoxymethylenemalonate (2.09 g) in DMF, the resultant mixture was stirred for 1 hour. After adding water, the liquid reaction mixture was extracted with a solvent mixture of ethyl acetate and n-hexane (3:2). The organic layer was washed with water and dried over anhydrous magnesium sulfate. After evaporating the solvent, IPE was added to the obtained residue and the mixture was stirred at 0° C. for 1 hour. The crystals thus precipitated were collected by filtration and the moist product thus obtained was dried under reduced pressure. Thus, the title compound (1.65 g, 99.8% ee) was obtained as colorless crystals. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 63.

후처리

  1. customthe liquid reaction mixture
  2. extractionwas extracted with a solvent mixture of ethyl acetate and n-hexane (3:2)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter evaporating the solvent, IPE
  6. additionwas added to the obtained residue
  7. customThe crystals thus precipitated
  8. filtrationwere collected by filtration
  9. customthe moist product thus obtained
  10. customwas dried under reduced pressure

출처 및 근거

ORD 기록
ord-ed8211677cac405d8fa028af6a5bb94f
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087778B2

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