Water → HCID 178500884, 화합물

HRID 50109

반응식

HRID 50109 반응식
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:7])=[CH:4][CH:3]=1.[C:15](#[N:19])[CH:16]([CH3:18])[CH3:17].[Sn](Cl)(Cl)(Cl)Cl.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH2:19][C:15]([CH:16]([CH3:18])[CH3:17])=[C:8]([C:6]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:14][CH:13]=1)=[O:7])[C:9]([O:11][CH3:12])=[O:10]

참가 물질

7

반응물 4

HCID 962WaterHCID 6559IsobutyronitrileHCID 24287Tin tetrachlorideHCID 579425Methyl 4-fluorobenzoylacetate

생성물 1

HCID 178500884HCID 178500884, 화합물수율 18,998.801%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

39.2 g of methyl 4-fluorobenzoylacetate (0.20 mmol) and 16.8 g of isobutyronitrile (0.24 mol, concentration >99%) were dissolved in 200 ml of toluene and treated with 57.9 g of tin tetrachloride (0.22 mmol, concentration >99%) at room temperature after the course of 10 minutes. After 30 min at room temperature, the mixture was heated to 80° C. After 8 h, the suspension was again cooled to room temperature and treated with 200 ml of water. The mixture was diluted with 200 ml of ethyl acetate and the phases were separated. The organic phase was washed twice with 40 ml of 1N sodium hydroxide solution and concentrated in vacuo (40° C./25 mbar) after drying over magnesium sulphate. 50.9 g of crude product were obtained in the form of a yellow oil. After chromatography of 12.0 g of crude product on silica gel (eluent: hexane/isopropanol 90:10), 10.08 g of methyl 3-amino-2-[1-(4-fluorophenyl)methanoyl]-4-methylpent-2-enoate were obtained in the form of a yellowish oil.

후처리

  1. waitAfter 8 h
  2. temperaturethe suspension was again cooled to room temperature
  3. customthe phases were separated
  4. washThe organic phase was washed twice with 40 ml of 1N sodium hydroxide solution
  5. concentrationconcentrated in vacuo (40° C./25 mbar)
  6. dry with materialafter drying over magnesium sulphate
  7. custom50.9 g of crude product were obtained in the form of a yellow oil

출처 및 근거

ORD 기록
ord-f6367908ef1d44ed8015b73da1427da5
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710178B2

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