Reaction #72093

Reaction equation

Methyl cis(±)-2-acetyl-4-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-oxobutanoate

Lawesson's reagent

Lawesson's reagent

→

title compound

Yield 7.3%

Methyl cis(±)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylthiophene-3-carboxylate

Yield 7.3%

Solvents

toluene

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at 110° C. for two hours
2. 2
   ConcentrationThe reaction solution was concentrated under reduced pressure
3. 3
   Otherthe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10)
4. 4
   Otherrecrystallized from methylene chloride/hexane

Procedure

Methyl cis(±)-2-acetyl-4-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-oxobutanoate obtained in Example (188b) (1.1 g) was dissolved in toluene. Lawesson's reagent (660 mg) was added, and the mixture was stirred at 110° C. for two hours. Further, Lawesson's reagent (330 mg) was added, and the mixture was stirred at 110° C. for two hours. The reaction solution was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10) and recrystallized from methylene chloride/hexane, to obtain 50 mg of the title compound as crystals.

Source