Water → HCID 178500884, 화합물

HRID 50108

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HRID 50108 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 59.8%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

5.00 g of methyl 4-fluorobenzoylacetate (24.2 mmol, concentration 95%) and 1.69 g of isobutyronitrile (24.2 mmol, concentration 98%) were dissolved in 25 ml of toluene and treated with 7.01 g of tin tetrachloride (26.6 mmol, concentration >99%) at room temperature after the course of 10 minutes. After 3 h at room temperature, the mixture was heated to 80° C. After 11.5 h, the suspension was again cooled to room temperature and treated with 25 ml of water. The mixture was diluted with 10 ml of ethyl acetate and the phases were separated. The organic phase was washed twice with 10 ml of 1N sodium hydroxide solution and concentrated in vacuo (40° C./25 mbar) after drying over magnesium sulphate. 6.18 g of crude product were obtained in the form of a yellow oil. After chromatography on silica gel (eluent: hexane/ethyl acetate 1.5:1), 3.84 g of methyl 3-amino-2-[1-(4-fluorophenyl)methanoyl]-4-methylpent-2-enoate were obtained in the form of an oil.

후처리

  1. waitAfter 11.5 h
  2. temperaturethe suspension was again cooled to room temperature
  3. customthe phases were separated
  4. washThe organic phase was washed twice with 10 ml of 1N sodium hydroxide solution
  5. concentrationconcentrated in vacuo (40° C./25 mbar)
  6. dry with materialafter drying over magnesium sulphate
  7. custom6.18 g of crude product were obtained in the form of a yellow oil

출처 및 근거

ORD 기록
ord-4d1657614f474eed850a97ba398cdfb1
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710178B2

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