HCID 70351673, compound → HCID 70353565, compound

HRID 1906773Notes

Reaction equation

HRID 1906773 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23]#[C:24][C:25]([O:27][CH3:28])=[O:26])=[C:10]1[C:29]([O:31][CH2:32][CH3:33])=[O:30].[H][H]>O1CCOCC1.[Pd]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:10]1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

5

Reactant 2

HCID 70351673HCID 70351673, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 70353565HCID 70353565, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}but-2-ynoate (1.00 g) in dioxane (30 ml) was stirred under one atmosphere (1.0333 kg.cm.-2) of hydrogen at room temperature in the presence of 5% palladium on barium sulphate. When the uptake of hydrogen had ceased the mixture was filtered and evaporated. The residue was purified by chromatography on silica (6 g) using toluene plus 0→50% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated and the residue crystallised from diisopropyl ether to give the title compound (0.40 g), m.p. 78°-80°.

Workup

  1. filtrationwas filtered
  2. customevaporated
  3. customThe residue was purified by chromatography on silica (6 g)
  4. customevaporated
  5. customthe residue crystallised from diisopropyl ether

Sources & evidence

ORD record
ord-49d8b84cfaa44e32a9ebb86130d266eb
Source dataset
uspto-grants-1987_03
Patent number
US04654353

Reaction notes

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