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

HRID 1995578Notes

Reaction equation

HRID 1995578 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-38a170fca28d48518fd0a926522659b6
Source dataset
uspto-grants-1983_09
Patent number
US04405530

Reaction notes

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