Water → 3-(4-Cyano-2-fluoro-phenyl)-5-methoxy-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester

HRID 1409710노트

반응식

HRID 1409710 반응식
[CH2:1](N(CC)CC)C.Cl[O:9][N:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=1[F:20].[CH3:21][O:22][C:23](=[CH2:27])[C:24]([O-:26])=[O:25].O>ClCCl>[CH3:1][O:25][C:24]([C:23]1([O:22][CH3:21])[O:9][N:10]=[C:11]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=2[F:20])[CH2:27]1)=[O:26]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 219344252-MethoxyacrylateHCID 866861574-Cyano-2-fluoro-benzaldehyde chlorooxime

생성물 1

HCID 866861563-(4-Cyano-2-fluoro-phenyl)-5-methoxy-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (1.05 mL) is added drop wise to a mixture of (4-cyano-2-fluoro-benzaldehyde chlorooxime (600 mg) and 2-methoxyacrylate (421 mg) in dichloromethane (7.5 mL). The reaction mixture is stirred over night at room temperature. Water is added and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→50:50) to afford the title compound. LC (method 18): tR=0.93 min; Mass spectrum (ESI+): m/z=279 [M+H]+.

후처리

  1. extractionthe aqueous phase is extracted with ethyl acetate
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→50:50)

출처 및 근거

ORD 기록
ord-33894cd5676e414ab8ff373753c24a41
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921398B2

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