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

HRID 1995578ノート

反応式

HRID 1995578 の反応式
[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]

参加物

6

反応物 4

HCID 6955Phthaloyl chlorideHCID 8471Triethylamine2 回HCID 18926764IsophthalimideHCID 20487154Methyl 2-amino-2-(fluoromethyl)pent-4-enoate

生成物 1

HCID 20487178Methyl 2-fluoromethyl-2-phthalimido-4-pentenoate収率 88%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-38a170fca28d48518fd0a926522659b6
出典データセット
uspto-grants-1983_09
特許番号
US04405530

反応ノート

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