tridecanoyl chloride

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

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

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: To a benzene solution containing 5.0 g (0.023 mol) of tridecanoic acid was added 25 g of thionyl chloride, followed by refluxing for 5 hours. The excess of thionyl chloride and benzene were removed by distillation to obtain tridecanoyl chloride. by refluxing for 5 hours The excess of thionyl chloride and benzene were removed by distillation

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

Procedure: {circle around (1)}: A solvent comprising 1.1 g of triethylamine and 5 g of toluene was added dropwise to a mixture comprising 2.28 g of benzyl 4-hydroxybenzoate, 2.33 g of n-tridecanoic chloride and 15 g of toluene in 30 minutes while cooling it with ice. After finishing adding dropwise, the mixture was stirred at room temperature for 3 hours. After finishing the reaction, deposited salts were filtered off, and the filtrate was neutralized with ½ N hydrochloric acid and washed with water. Then, toluene was distilled off under reduced pressure, and the resultant residue was recrystallized from ethanol, whereby 3.52 g of benzyl 4-n-dodecylcarbonyloxybenzoate was obtained in the form of a colorless crystal. while cooling it with ice After finishing adding dropwise the reaction were filtered off washed with water Then, toluene was distilled off under reduced pressure the resultant residue was recrystallized from ethanol

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

Procedure: Tridecanoyl chloride (15.08 g, 0.061 mol) was added to a mixture of α-[(hydroxyamino)iminomethyl]-N-(2,4,6-trimethoxyphenyl)-benzene acetamide (19.8 g, 0.055 mol), Hunig's base (10.6 mL, 0.061 mol), and THF (200 mL). The mixture was stirred in THF at room temperature for 2 hours, then concentrated in vacuo and dissolved in glacial acetic acid (50 mL) and refluxed for 2 hours, then concentrated in vacuo, azeotroped with toluene (2×250 mL), and columned on silica gel eluting with 35% ethyl acetate in hexanes to yield a white solid (12.1 g, 62%). %(found): C, 68.93; H, 7.96; N, 7.54. concentrated in vacuo dissolved in glacial acetic acid (50 mL) refluxed for 2 hours concentrated in vacuo azeotroped with toluene (2×250 mL)

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

Procedure: Tridecanoyl chloride (15.08 g, 0.061 mol) was added to a mixture of α-[(hydroxyamino)iminomethyl]-N-(2,4,6-trimethoxyphenyl)-benzene acetamide (19.8 g, 0.055 mol), Hunig's base (10.6 mL, 0.061 mol), and THF (200 mL). The mixture was stirred in THF at room temperature for 2 hours, then concentrated in vacuo and dissolved in glacial acetic acid (50 mL) and refluxed for 2 hours, then concentrated in vacuo, azeotroped with toluene (2×250 mL), and columned on silica gel eluting with 35% ethyl acetate in hexanes to yield a white solid (12.1 g, 62%). %(found): C, 68.93; H, 7.96; N, 7.54. concentrated in vacuo dissolved in glacial acetic acid (50 mL) refluxed for 2 hours concentrated in vacuo azeotroped with toluene (2×250 mL)

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

Procedure: To a solution of 2-fluoro-4-hydroxybenzoic acid (1.4 g) and triethylamine (1.0 g) in dichloromethane (40 ml) were added tridecanoyl chloride (2.0 g) and dimethylaminopyridine (0.2 g). The solution was stirred at room temperature for about 20 hours and thereto was added dilute aqueous hydrochloric acid solution. The organic layer was separated by a funnel and distilled to remove the solvent. The residue was washed with n-hexane and dried to obtain the titled compound (about 1.8 g). The organic layer was separated by a funnel distilled to remove the solvent The residue was washed with n-hexane dried

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

Procedure: To a solution of 2-fluoro-4-hydroxybenzoic acid (1.4 g) and triethylamine (1.0 g) in dichloromethane (40 ml) were added tridecanoyl chloride (2.0 g) and dimethylaminopyridine (0.2 g). The solution was stirred at room temperature for about 20 hours and thereto was added dilute aqueous hydrochloric acid solution. The organic layer was separated by a funnel and distilled to remove the solvent. The residue was washed with n-hexane and dried to obtain the titled compound (about 1.8 g). The organic layer was separated by a funnel distilled to remove the solvent The residue was washed with n-hexane dried

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

Procedure: To a solution (20 ml) of 2.78 g (20 mmol) of ethyl pyrrole-3-carboxylate in benzene was added tridecanoyl chloride prepared from 4.28 g (20 mml) of tridecanoic acid in a conventional manner, followed by further dropwise addition of 3.5 ml (30 mmol) of stannic chloride. After the addition, the mixture was stirred for 15 hours at room temperature, treated with diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the residue was purified by subjecting it to silica gel column chromatography (eluent: ethyl acetate/hexane=1/7) to obtain 4.85 g (72% yield) of ethyl 5-tridecanoylpyrrole-3-carboxylate. After the addition extracted with ethyl acetate The extract was washed with water dried over anhydrous magnesium sulfate After removing the solvent under reduced pressure the residue was purified

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

Procedure: N-tridecanoyl tyramine was prepared by adding dropwise about 2.80 ml of tridecanoyl chloride to a cooled solution comprising about 1 g of tyramine and about 1.52 ml of triethylamine in THF. The reaction mixture was stirred at room temperature for 48 hours. The mixture was then poured into about 70 ml of a 10% HCl solution and the mixture extracted with ethyl acetate (3×50 ml). The ethyl acetate layer was separated, dried (Na2SO4) and concentrated under reduced pressure to yield about 2 g of crude N-tridecanoyl tyramine. The product was purified by chromatography on a silica gel column eluted with methylene chloride/ethyl acetate (30:1). About 1 g of N-tridecanoyl tyranine was added to a stirred solution comprising about 152 mg of N-tridecanoyl tyramine, sodium hydroxide in 20 ml anhydrous DMF at 0° C. under nitrogen. The solution was stirred for 30 minutes; about 1 g of chlorosulfonamide was slowly added in one portion. The solution was then stirred at room temperature for 24 hours. After this time, the mixture was poured into a cold saturated sodium bicarbonate solution and the resulting solution was extracted with methylene chloride (3×50 ml). The organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure to yield about 677 mg of product, which was then purified by chromatography on a silica gel column eluted with methylene chloride/ethyl acetate (20:1). The product produced is (p-o-sulfamoyl)-N-tridecanoyl tyramine. N-tridecanoyl tyramine was prepared the mixture extracted with ethyl acetate (3×50 ml) The ethyl acetate layer was separated dried (Na2SO4) concentrated under reduced pressure