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

HRID 1789018Notes

Reaction equation

HRID 1789018 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][CH2:16][CH2:15]1)=[O:12].[NH2:21][C:22]([CH2:28][F:29])=[CH:23][C:24]([O:26][CH3:27])=[O:25]>C(OCC)(=O)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][CH2:16][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 54003830Cyclobutyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoateHCID 73668923Methyl 3-amino-4-fluoro-2-butenoate

Product 1

HCID 700897525-Cyclobutyl 3-methyl 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of step (a) (1.7 g, 5.4 mmoles) and methyl 3-amino-4-fluoro-2-butenoate (0.72 g, 5.4 mmoles) were mixed and heated to 95° (oil bath temperature) under an atmosphere of nitrogen for 6 hours. The oil was allowed to cool to room temperature. Chromatography on silica eluting with petroleum ether (60°-80° )/ethyl acetate mixtures, afforded the title compound as a yellow solid, which was recrystallised from petroleum ether (60°-80° ) to afford the title compound 0.37 g, mp 148°-9°.

Workup

  1. temperatureheated to 95° (oil bath temperature) under an atmosphere of nitrogen for 6 hours

Sources & evidence

ORD record
ord-6f215c3459dd4856a60fd10a38793d91
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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