(3-Oxetanyl) 2-(2,3-dichlorophenylmethylene)-3-oxobutanoate → 3-Methyl 5-(3-oxetanyl) 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate

HRID 1789020Notes

Reaction equation

HRID 1789020 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]=[C:10]([C:18](=O)[CH3:19])[C:11]([O:13][CH:14]1[CH2:17][O:16][CH2:15]1)=[O:12].[NH2:21][C:22]([CH2:28][F:29])=[CH:23][C:24]([O:26][CH3:27])=[O:25]>C(O)(C)(C)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:10]([C:11]([O:13][CH:14]2[CH2:17][O:16][CH2:15]2)=[O:12])=[C:18]([CH3:19])[NH:21][C:22]([CH2:28][F:29])=[C:23]1[C:24]([O:26][CH3:27])=[O:25]

Participants

4

Reactant 2

HCID 57031759(3-Oxetanyl) 2-(2,3-dichlorophenylmethylene)-3-oxobutanoateHCID 73668923Methyl 3-amino-4-fluoro-2-butenoate

Product 1

HCID 700876883-Methyl 5-(3-oxetanyl) 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of the product of step (a) (2.9 g, 7.6 mmoles) and methyl 3-amino-4-fluoro-2-butenoate (1 g, 7.6 mmoles) in dry tert-butanol (20 ml) was heated to 60° (oil bath temperature) for 16 hours. The solution was allowed to cool to room temperature and the solvent removed in vacuo. Chromatography on silica, eluting with dichloromethane/ethyl acetate mixtures afforded the title compound as an oil which crystallised on addition of petroleum ether (60°-80° ). The solid was recrystallised from petroleum ether (60°-80° )/acetone to afford the title compound 1.03 g, mp 155°-6°.

Workup

  1. customthe solvent removed in vacuo
  2. washChromatography on silica, eluting with dichloromethane/ethyl acetate mixtures

Sources & evidence

ORD record
ord-3c7b27071d2a4a3aac8df5aa0a19735f
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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