(2,5-dioxopyrrolidin-1-yl) hexadecanoate

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

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

Procedure: A total amount (260.3 g) of N-palmitoyloxy-succinimide synthesized above was suspended in 750 ml of DMF. To the suspension, a solution of Gly (56.3 g, 0.750 mol) and triethylamine (83.2 ml, 0.598 mol) in 250 ml of water was added dropwise with stirring while cooling with ice. The whole was stirred for 30 minutes while cooled with ice, then allowed to gradually reach room temperature, and stirred for 15 hours. An aqueous solution with pH 3 that was prepared by dissolving 100 ml of 6N hydrochloric acid in 1 L of water was stirred while cooled with ice. The reaction solution containing N-palmitoyloxy-succinimide was added dropwise to the aqueous solution. The precipitated solid was collected by filtration. The precipitated solid was washed with 2 L of water and then 1 L of hexane, and recovered to give 114 g (67%) of a target compound. while cooling with ice The whole was stirred for 30 minutes while cooled with ice allowed to gradually reach room temperature stirred for 15 hours An aqueous solution with pH 3 that was prepared was stirred while cooled with ice was added dropwise to the aqueous solution The precipitated solid was collected by filtration The precipitated solid was washed with 2 L of water 1 L of hexane, and recovered

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

Procedure: N-hydroxysuccinimide (69.8 g, 0.598 mol) was added drop by drop to 1 L of chloroform solution of palmitoyl chloride (165 ml, 0.544 mol) with stirring while cooling with ice, and then triethylamine (83.1 ml, 0.598 mol) was added dropwise over 30 minutes. Then, the whole was stirred while cooled with ice for 30 minutes, allowed to gradually reach room temperature, and stirred for 7 hours. The reaction mixture was washed with water (500 ml×3), then dried over magnesium sulfate, and concentrated under reduced pressure to give 260.3 g (quant) of a colorless solid. while cooling with ice Then, the whole was stirred while cooled with ice for 30 minutes allowed to gradually reach room temperature stirred for 7 hours The reaction mixture was washed with water (500 ml×3) dried over magnesium sulfate concentrated under reduced pressure to give 260.3 g (quant) of a colorless solid

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

Procedure: To the solution of L-lysine (1 mmol) in water (2 ml) and triethylamine (0.27 ml, 2 mmol) 1 mmol of succinimidyl palmitate (suspended in 2 ml of acetone) was added at room temperature under stirring. Stirring of the reaction mixture was continued for 4h. Triethylamine was removed under reduced pressure, the precipitate was collected by filtration, washed with water and ethanol, crystallized from glacial acetic acid giving an 86% yield of the title compound. Analysis data are given in Table 2. Stirring of the reaction mixture Triethylamine was removed under reduced pressure the precipitate was collected by filtration washed with water and ethanol

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

Procedure: 260.3 g of the N-palmitoyloxy-succinimide synthesized above as a whole was suspended in 750 ml of DMF and, to the resultant solution while cooled with ice with stirring, 56.3 g (0.750 mol) of Gly and 83.2 mL (0.598 mol) of triethylamine dissolved in 250 ml of water were added dropwise. The resultant solution was stirred for another 30 minutes while cooled with ice and for another 15 hours during which the resultant solution gradually reached room temperature. To an aqueous solution obtained by dissolving 100 mL of 6 N hydrochloric acid in 1 L of water and adjusting the pH to pH 3, while cooled with ice with stirring, the reaction solution was added dropwise to precipitate a solid, which was filtered off. The resultant product was washed with 2 L of water and then with 1 L of hexane, and was then collected to obtain 114 g (67%) of a desired compound. while cooled with ice were added dropwise To an aqueous solution obtained while cooled with ice with stirring the reaction solution was added dropwise to precipitate a solid, which was filtered off The resultant product was washed with 2 L of water with 1 L of hexane, and was then collected

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

Procedure: To a solution of 165 mL (0.544 mol) of palmitoyl chloride in 1 L of chloroform while cooled with ice with stirring, 69.8 g (0.598 mol) of N-hydroxysuccinimide was gradually added, and 83.1 mL (0.598 mol) of triethylamine was added dropwise thereto over 30 minutes. The resultant solution was stirred for 30 minutes while cooled with ice and for another 7 hours during which the resultant solution gradually reached room temperature. After washed with 500 mL of water three times, the resultant solution was dried over magnesium sulfate and was then concentrated under reduced pressure to obtain 260.3 g (quant) of a colorless solid. After washed with 500 mL of water three times the resultant solution was dried over magnesium sulfate was then concentrated under reduced pressure to obtain 260.3 g (quant) of a colorless solid

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

Procedure: A total amount (260.3 g) of N-palmitoyloxy-succinimide synthesized above was suspended in 750 ml of DMF. To the suspension, a solution of Gly (56.3 g, 0.750 mol) and triethylamine (83.2 ml, 0.598 mol) in 250 ml of water was added dropwise with stirring while cooling with ice. The whole was stirred for 30 minutes while cooled with ice, then allowed to gradually reach room temperature, and stirred for 15 hours. An aqueous solution with pH 3 that was prepared by dissolving 100 ml of 6N hydrochloric acid in 1 L of water was stirred while cooled with ice. The reaction solution containing N-palmitoyloxy-succinimide was added dropwise to the aqueous solution. The precipitated solid was collected by filtration. The precipitated solid was washed with 2 L of water and then 1 L of hexane, and recovered to give 114 g (67%) of a target compound. while cooling with ice The whole was stirred for 30 minutes while cooled with ice allowed to gradually reach room temperature stirred for 15 hours An aqueous solution with pH 3 that was prepared was stirred while cooled with ice was added dropwise to the aqueous solution The precipitated solid was collected by filtration The precipitated solid was washed with 2 L of water 1 L of hexane, and recovered

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

Procedure: N-hydroxysuccinimide (69.8 g, 0.598 mol) was added drop by drop to 1 L of chloroform solution of palmitoyl chloride (165 ml, 0.544 mol) with stirring while cooling with ice, and then triethylamine (83.1 ml, 0.598 mol) was added dropwise over 30 minutes. Then, the whole was stirred while cooled with ice for 30 minutes, allowed to gradually reach room temperature, and stirred for 7 hours. The reaction mixture was washed with water (500 ml×3), then dried over magnesium sulfate, and concentrated under reduced pressure to give 260.3 g (quant) of a colorless solid. while cooling with ice Then, the whole was stirred while cooled with ice for 30 minutes allowed to gradually reach room temperature stirred for 7 hours The reaction mixture was washed with water (500 ml×3) dried over magnesium sulfate concentrated under reduced pressure to give 260.3 g (quant) of a colorless solid