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

HRID 8469

반응식

HRID 8469 반응식
[F:1][C:2]1[C:12]([F:13])=[C:11]([F:14])[CH:10]=[CH:9][C:3]=1[NH:4][C@@H:5]([CH3:8])[CH2:6][OH:7].C(O[CH:18]=[C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])C.C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC.ClCCl>[F:1][C:2]1[C:12]([F:13])=[C:11]([F:14])[CH:10]=[CH:9][C:3]=1[N:4]([CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C@@H:5]([CH3:8])[CH2:6][OH:7]

참가 물질

6

반응물 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanol

생성물 1

HCID 11485652Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate수율 78.4%

시약·촉매·용매 2

HCID 80021Tetrahexylammonium chloride촉매HCID 6344Dichloromethane용매

실험 절차

The compound (103 mg) obtained in Example 51, diethyl ethoxymethylenemalonate (108 mg) and tetrahexylammonium chloride (29 mg) were dissolved in dichloromethane (1 ml). After adding potassium carbonate (138 mg), the mixture was stirred at room temperature for 22 hours. After the completion of the reaction, the residue was filtered off and the solvent was evaporated. Then the residue thus obtained was subjected to silica gel column chromatography to thereby give 147 mg (78%) of the title compound as a colorless solid. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 63.

후처리

  1. customAfter the completion of the reaction
  2. filtrationthe residue was filtered off
  3. customthe solvent was evaporated
  4. customThen the residue thus obtained

출처 및 근거

ORD 기록
ord-05a1c88e83fc4495b20a55fb1c3be8ed
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087778B2

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