1-octylpyrrole-2,5-dione

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

Procedure: A mixture of N-octyl maleimide (0.01 M) prepared as described in Example 10 above, octylamine (0.01 M), triethylamine [catalytic, 0.1 equivalent] in acetonitrile (25 ml) was stirred for 24 hours at room temperature. Acetonitrile was removed under vacuum to leave a residual liquid product which was flash chromatographed (25% ethyl acetate in petroleum ether) to yield a white solid as the desired product. prepared Acetonitrile was removed under vacuum to leave a residual liquid product which chromatographed (25% ethyl acetate in petroleum ether)

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of maleic anhydride (54, 5.4 g, 55 mmol) in 150 ml of benzene, a solution of octyl amine (53, 6.46 g, 50 mmol) in 100 ml of benzene was added. The resulting mixture was stirred at 30° C. for an hour and ZnBr2 (12.4 g, 55 mmol) and hexamethyl disilazane (12.1 g, 75 mmol) in 30 ml of benzene were added. The resulting suspension was refluxed for 2 hrs. After cooling to room temperature, the reaction mixture was poured into 200 ml of 0.5 M HCl. The organic layer was separated and the aqueous portion was extracted twice with 150 ml portions of EtOAc. The combined organic layers were washed with saturated aqueous NaHCO3 (2×150 ml), brine (1×150 ml), and dried over Na2SO4. The solution was dried under vacuum to yield an oily product which solidified gradually to yield the cream colored solid product (9.2 g, 88%). 1H NMR (300 MHz, CDCl3): δ 0.87 (t, 3H, J=6 Hz), 1.20-1.40 (m, 10H), 1.50-1.70 (m, 2H), 3.51 (t, 2H, J=6 Hz), 6.69 (s, 2H). The resulting suspension was refluxed for 2 hrs After cooling to room temperature The organic layer was separated the aqueous portion was extracted twice with 150 ml portions of EtOAc The combined organic layers were washed with saturated aqueous NaHCO3 (2×150 ml), brine (1×150 ml) dried over Na2SO4 The solution was dried under vacuum to yield an oily product which

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

Procedure: For a vehicle control, combine a solution of vehicle (5 mM NaPO4 pH 5.5, 150 mM NaCl, 0.5 mM DTT) with PBS (Gibco product # 20012-027, pH 7.2) in a 3:7 ratio. Add 1/400 vol. of 60 mM octylmaleimide in DMSO and a 1/400 vol. of DMSO to give a final concentration of 150 μM N-octylmaleimide and 0.5% DMSO. Finally, add 1:1000 vol. of 0.5 M DTT.

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

Procedure: For a vehicle control, combine a solution of vehicle (5 mM NaPO4 pH 5.5, 150 mM NaCl, 0.5 mM DTT) with PBS (Gibco product # 20012-027, pH 7.2) in a 1:10 ratio. Add 1/400 vol. of 20 mM octylmaleimide in DMSO and a 1/400 vol. of DMSO to give a final concentration of 50 μM N-octylmaleimide and 0.5% DMSO. Finally, add 1:1000 vol. of 0.35 M DTT.

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

Procedure: Into a sealed glass tube were introduced 26 g of N-n-octylmaleimide, 2.4 g of maleic anhydride, and 0.036 g of dimethyl-2,2′-azobisisobutyrate as a polymerization initiator. After nitrogen displacement, a radical polymerization reaction was conducted under the conditions of a polymerization temperature of 60° C. and a polymerization time of 5 hours. Chloroform was added after the reaction to obtain a polymer solution. Thereafter, this solution was mixed with excess methanol to thereby precipitate the polymer. The polymer obtained was taken out by filtration, subsequently sufficiently washed with methanol, and dried at 80° C. Thus, an N-n-octylmaleimide-maleic anhydride copolymer resin was obtained in an amount of 19 g. The N-n-octylmaleimide-maleic anhydride copolymer resin obtained contained a maleic anhydride residue in an amount of 20% by weight and had a number-average molecular weight of 140,000. After nitrogen displacement, a radical polymerization reaction was conducted under the conditions of a polymerization temperature of 60° C. a polymerization time of 5 hours after the reaction to obtain a polymer solution to thereby precipitate the polymer The polymer obtained was taken out by filtration subsequently sufficiently washed with methanol dried at 80° C

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

Procedure: Into a sealed glass tube were introduced 26 g of N-n-octylmaleimide, 4.8 g of maleic anhydride, and 0.04 g of dimethyl-2,2′-azobisisobutyrate as a polymerization initiator. After nitrogen displacement, a radical polymerization reaction was conducted under the conditions of a polymerization temperature of 60° C. and a polymerization time of 5 hours. Chloroform was added after the reaction to obtain a polymer solution. Thereafter, this solution was mixed with excess methanol to thereby precipitate the polymer. The polymer obtained was taken out by filtration, subsequently sufficiently washed with methanol, and dried at 80° C. Thus, an N-n-octylmaleimide-maleic anhydride copolymer resin was obtained in an amount of 18 g. The N-n-octylmaleimide-maleic anhydride copolymer resin obtained contained maleic anhydride residue unit in an amount of 20% by weight and had a number-average molecular weight of 140,000. After nitrogen displacement, a radical polymerization reaction was conducted under the conditions of a polymerization temperature of 60° C. a polymerization time of 5 hours after the reaction to obtain a polymer solution to thereby precipitate the polymer The polymer obtained was taken out by filtration subsequently sufficiently washed with methanol dried at 80° C

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

Procedure: Into a sealed glass tube were introduced 26 g of N-n-octylmaleimide, 4.8 g of maleic anhydride, and 0.04 g of dimethyl-2,2′-azobisisobutyrate as a polymerization initiator. After nitrogen displacement, a radical polymerization reaction was conducted under the conditions of a polymerization temperature of 60° C. and a polymerization time of 5 hours. Chloroform was added after the reaction to obtain a polymer solution. Thereafter, this solution was mixed with excess methanol to thereby precipitate the polymer. The polymer obtained was taken out by filtration, subsequently sufficiently washed with methanol, and dried at 80° C. Thus, an N-n-octylmaleimide-maleic anhydride copolymer resin was obtained in an amount of 18 g. The N-n-octylmaleimide-maleic anhydride copolymer resin obtained contained maleic anhydride residue unit in an amount of 40% by weight and had a number-average molecular weight of 140,000. After nitrogen displacement, a radical polymerization reaction was conducted under the conditions of a polymerization temperature of 60° C. a polymerization time of 5 hours after the reaction to obtain a polymer solution to thereby precipitate the polymer The polymer obtained was taken out by filtration subsequently sufficiently washed with methanol dried at 80° C

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

Procedure: Into a sealed glass tube were introduced 26 g of N-n-octylmaleimide, 2.4 g of maleic anhydride, and 0.036 g of dimethyl-2,2′-azobisisobutyrate as a polymerization initiator. After nitrogen displacement, a radical polymerization reaction was conducted under the conditions of a polymerization temperature of 60° C. and a polymerization time of 5 hours. Chloroform was added after the reaction to obtain a polymer solution. Thereafter, this solution was mixed with excess methanol to thereby precipitate the polymer. The polymer obtained was taken out by filtration, subsequently sufficiently washed with methanol, and dried at 80° C. Thus, an N-n-octylmaleimide-maleic anhydride copolymer resin was obtained in an amount of 19 g. The N-n-octylmaleimide-maleic anhydride copolymer resin obtained contained a maleic anhydride residue in an amount of 20% by weight and had a number-average molecular weight of 120,000. After nitrogen displacement, a radical polymerization reaction was conducted under the conditions of a polymerization temperature of 60° C. a polymerization time of 5 hours after the reaction to obtain a polymer solution to thereby precipitate the polymer The polymer obtained was taken out by filtration subsequently sufficiently washed with methanol dried at 80° C

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of maleic anhydride (3.0 g, 30.6 mmol) in 80 mL of benzene, a solution of octylamine (3.59 g, 27.8 mmol) in 50 mL of benzene was added. The resulting mixture was stirred at 30° C. for an hour and zinc bromide (ZnBr2, 6.89 g, 30.6 mmol) and hexamethyl disilazane (6.72 g, 41.7 mmol) in 20 mL of benzene were added. The resulting suspension was heated under reflux for 2 hours. After cooling to room temperature, the reaction mixture was poured into 200 mL of 0.5 M hydrochloric acid (HCl). The organic layer was separated and the aqueous portion was extracted twice with 150 mL portions of ethyl acetate (EtOAc). The combined organic layers were washed with saturated aqueous sodium bicarbonate (NaHCO3, 2×150 mL), brine (1×150 mL), and dried over magnesium sulfate (MgSO4). The solution was concentrated under vacuum to yield a viscous solid, which is subsequently sublimed to produce N-octylmaleimide as a white solid (4.8 g, 92%). 1H NMR (400 MHz, CDCl3): δ 0.87 (t, 3H, J=6 Hz), 1.20-1.40 (m, 10H), 1.50-1.70 (m, 2H), 3.51 (t, 2H, J=6 Hz), 6.69 (s, 2H). The resulting suspension was heated under reflux for 2 hours After cooling to room temperature The organic layer was separated the aqueous portion was extracted twice with 150 mL portions of ethyl acetate (EtOAc) The combined organic layers were washed with saturated aqueous sodium bicarbonate (NaHCO3, 2×150 mL), brine (1×150 mL) dried over magnesium sulfate (MgSO4) The solution was concentrated under vacuum to yield a viscous solid, which

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

Procedure: For a vehicle control, combine a solution of vehicle (5 mM NaPO4 pH 5.5, 150 mM NaCl, 0.5 mM DTT) with PBS (Gibco product #20012-027, pH 7.2) in a 3:7 ratio. Add 1/400 vol. of 60 mM octylmaleimide in DMSO and a 1/400 vol. of DMSO to give a final concentration of 150 μM N-octylmaleimide and 0.5% DMSO. Finally, add 1:1000 vol. of 0.5 M DTT.

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

Procedure: For a vehicle control, combine a solution of vehicle (5 mM NaPO4 pH 5.5, 150 mM NaCl, 0.5 mM DTT) with PBS (Gibco product #20012-027, pH 7.2) in a 1:10 ratio. Add 1/400 vol. of 20 mM Octylmaleimide in DMSO and a 1/400 vol. of DMSO to give a final concentration of 50 μM N-octylmaleimide and 0.5% DMSO. Finally, add 1:1000 vol. of 0.35 M DTT.

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

Procedure: A mixture of N-octyl maleimide (0.01 M) prepared as described in Example 10 above, octylamine (0.01 M), triethylamine [catalytic, 0.1 equivalent] in acetonitrile (25 ml) was stirred for 24 hours at room temperature. Acetonitrile was removed under vacuum to leave a residual liquid product which was flash chromatographed (25% ethyl acetate in petroleum ether) to yield a white solid as the desired product. prepared Acetonitrile was removed under vacuum to leave a residual liquid product which chromatographed (25% ethyl acetate in petroleum ether)