Decanoic acid, 2,5-dioxo-1-pyrrolidinyl ester

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

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

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

Procedure: Similarly, as in example 2, the title compound was prepared using L-lysine monohydrochloride (7.30 g, 40 mmol) and succinimidyl caprate (10.7 g, 40 mmol) in the presence of triethylamine (16.8 ml, 120 mmol) in 35 ml of water and 36 ml of acetone. The product was washed with cold water and with cold ethanol then dried giving 9.04 g (78%) of the desired compound. Infrared: 1580-1590 cm-1 (ionized carboxyl), 1520-1540 and 1640 cm-1 (amide bands). Similarly, as in example 2, the title compound was prepared The product was washed with cold water and with cold ethanol then dried

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

Procedure: A solution of decanoyl chloride (5.0 g) in tetrahydrofuran (20 ml) was dropwise added to a mixture of N-hydroxysuccinimide (3.06 g) and triethylamine (3.7 ml) in tetrahydrofuran (30 ml) with stirring under ice-cooling. The mixture was stirred at the same temperature for one hour and then at ambient temperature for 15 hours. A precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (50 ml). The solution was washed with water (50 ml), dried over magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to give N-decanoyloxysuccinimide as a crystal (4.95 g). cooling The mixture was stirred at the same temperature for one hour A precipitate was filtered off the filtrate was concentrated under reduced pressure The residue was dissolved in ethyl acetate (50 ml) The solution was washed with water (50 ml) dried over magnesium sulfate concentrated under reduced pressure The residue was crystallized from ethyl acetate-hexane