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

HRID 1789016Notes

Reaction equation

HRID 1789016 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:19](=O)[CH3:20])[C:11]([O:13][CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12].[NH2:22][C:23]([CH2:29][F:30])=[CH:24][C:25]([O:27][CH3:28])=[O:26]>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[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:12])=[C:19]([CH3:20])[NH:22][C:23]([CH2:29][F:30])=[C:24]1[C:25]([O:27][CH3:28])=[O:26]

Participants

4

Reactant 2

HCID 54059666Cyclopentyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoateHCID 73668923Methyl 3-amino-4-fluoro-2-butenoate

Product 1

HCID 700905275-Cyclopentyl 3-methyl 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) (5.1 g, 14.3 mmoles) and methyl 3-amino-4-fluoro-2-butenoate (1.9 g, 14.3 mmoles) in dry tert-butanol (25 ml) was heated to 60° (oil bath temperature) for 108 hours. The solution was allowed to cool to room temperature and the solvent removed in vacuo. Chromatography on silica eluting with dichloromethane afforded the title compound as a yellow oil which crystallises on addition of petroleum ether (60°-80° ) to afford the title compound 1.5 g mp 148°-9°. (Identical with the product of Example 3).

Workup

  1. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a018ff87fe284e27a01f07bd10715329
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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