Phthaloyl chloride → Methyl 2-fluoromethyl-2-phthalimido-4-pentenoate

HRID 1995578노트

반응식

HRID 1995578 반응식
[F:1][CH2:2][C:3]([NH2:11])([CH2:8][CH:9]=[CH2:10])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[C:19](Cl)(=[O:29])[C:20]1[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:22](Cl)=[O:23].C1(=O)NC(=O)C2=CC=CC1=C2>ClCCl>[F:1][CH2:2][C:3]([N:11]1[C:22](=[O:23])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]2[C:19]1=[O:29])([CH2:8][CH:9]=[CH2:10])[C:4]([O:6][CH3:7])=[O:5]

참가 물질

6

반응물 4

HCID 6955Phthaloyl chlorideHCID 8471Triethylamine2회HCID 18926764IsophthalimideHCID 20487154Methyl 2-amino-2-(fluoromethyl)pent-4-enoate

생성물 1

HCID 20487178Methyl 2-fluoromethyl-2-phthalimido-4-pentenoate수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of methyl 2-fluoromethyl-2-amino-4-pentenoate (2.10 g, 13 mmol) and triethylamine (3 g) in dry dichloromethane, phthaloyl dichloride (2.37 g, 11.7 mmol) is added with ice cooling. After stirring overnight, at room temperature, the solution is washed with water and 1 N HCl. Drying and removal of solvent by evaporation gives a residue, consisting mainly of the iso-phthalimide. The residue is dissolved in dry dichloromethane, two equivalents of triethylamine are added, and the mixture is refluxed overnight. Work-up as described above gives the title compound as an oil (3.0 g).

후처리

  1. washthe solution is washed with water and 1 N HCl
  2. customDrying
  3. customremoval of solvent
  4. customby evaporation
  5. customgives a residue
  6. temperaturethe mixture is refluxed overnight

출처 및 근거

ORD 기록
ord-38a170fca28d48518fd0a926522659b6
출처 데이터셋
uspto-grants-1983_09
특허 번호
US04405530

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