diethyl 2-benzamidopropanedioate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 5 ml of dry ethanol, 675 mg of 20% sodium ethoxide-ethanol solution and 698 mg of diethyl benzoylaminomalonate were added, and stirred for 30 minutes at room temperature. Then, a solution of 914 mg of methyl 6-bromohexyloxy-2-methylpropionate/4 ml of dry ethanol was added dropwise, and stirred for 15 hours at 50-60° C. The reaction solution was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=5:1) to provide 642 mg of the objective compound as yellowish oil. stirred for 15 hours at 50-60° C The reaction solution was poured into ice-cold water extracted with ethyl acetate The organic layer was washed with brine dried over anhydrous magnesium sulfate concentrated The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=5:1)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution comprised of sodium iodide (7.9 g, 52.7 mmol) and 2-chloroethyl phenyl sulfide (4.7 g, 27.2 mmol) in acetone (40 mL) was refluxed for 15 hours. The reaction mixture was cooled, diluted with ice water and extracted with ethyl acetate. The extract was concentrated and the residue was combined with N-methylpyrrolidone (20 mL), lithium hydroxide (1.6 g, 67 mmol) and diethyl 2-benzoylaminomalonate (5 g, 18 mmol). The mixture was stirred at ambient temperature of 15 hours and then poured into cold water. The product was extracted with ethyl acetate and purified by silica gel chromatography to provide diethyl 2-benzoylamino-2-(2-phenylsulfanylethyl)malonate (1.316 g, 3.2 mmol). was refluxed for 15 hours The reaction mixture was cooled extracted with ethyl acetate The extract was concentrated The product was extracted with ethyl acetate purified by silica gel chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution comprised of sodium iodide (7.9 g, 52.7 mmol) and 2-chloroethyl phenyl sulfide (4.7 g, 27.2 mmol) in acetone (40 mL) was refluxed for 15 hours. The reaction mixture was cooled, diluted with ice water and extracted with ethyl acetate. The extract was concentrated and the residue was combined with N-methylpyrrolidone (20 mL), lithium hydroxide (1.6 g, 67 mmol) and diethyl 2-benzoylaminomalonate (5 g, 18 mmol). The mixture was stirred at ambient temperature of 15 hours and then poured into cold water. The product was extracted with ethyl acetate and purified by silica gel chromatography to provide diethyl 2-benzoylamino-2-(2-phenylsulfanylethyl)malonate (1.316 g, 3.2 mmol). was refluxed for 15 hours The reaction mixture was cooled extracted with ethyl acetate The extract was concentrated The product was extracted with ethyl acetate purified by silica gel chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 5 ml of dry ethanol, 675 mg of 20% sodium ethoxide-ethanol solution and 698 mg of diethyl benzoylaminomalonate were added, and stirred for 30 minutes at room temperature. Then, a solution of 914 mg of methyl 6-bromohexyloxy-2-methylpropionate/4 ml of dry ethanol was added dropwise, and stirred for 15 hours at 50–60° C. The reaction solution was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=5:1) to provide 642 mg of the objective compound as yellowish oil. stirred for 15 hours at 50–60° C The reaction solution was poured into ice-cold water extracted with ethyl acetate The organic layer was washed with brine dried over anhydrous magnesium sulfate concentrated The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=5:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 5 ml of dry ethanol, 675 mg of 20% sodium ethoxide-ethanol solution and 698 mg of diethyl benzoylaminomalonate were added, and stirred for 30 minutes at room temperature. Then, a solution of 914 mg of methyl 6-bromohexyloxy-2-methylpropionate/4 ml of dry ethanol was added dropwise, and stirred for 15 hours at 50-60° C. The reaction solution was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=5:1) to provide 642 mg of the objective compound as yellowish oil. stirred for 15 hours at 50-60° C The reaction solution was poured into ice-cold water extracted with ethyl acetate The organic layer was washed with brine dried over anhydrous magnesium sulfate concentrated The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=5:1)