tetradecanoyl 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:; See reaction.notes.procedure_details.

Procedure: To a 25 mL round-bottomed flask equipped with a magnetic stir bar was added 2-azidoethanamine (0.102 g, 1.18 mmol), DCM (5 mL) and then triethylamine (0.239 g, 2.37 mmol). To this reaction mixture, tetradecanoyl chloride (0.292 g, 1.18 mmol) was added dropwise and allowed to stir at room temperature for 24 hr. Then, the reaction mixture was concentrated de vacuo and then purified via silica gel column chromatography (100% dichloromethane to 1:40 methanol:dichloromethane) to give N-(2-azidoethyl)tetradecanamide (0.245 g, 79% yield). 1H NMR (300 MHz, CDCl3) δ 5.86 (s, 1H), S 3.42 (s, 4H), δ 2.18 (t, 2H), δ 1.62 (m, 2H), δ 1.24 (m, 20H), δ 0.87 (t, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 173.7, 51.2, 39.1, 36.9, 32.1, 29.9, 29.8, 29.7, 29.6, 29.5, 25.9, 22.9, 14.4 ppm; HRMS (ESI) calcd for C16H32N4O (M+) 296.2576, found 296.2566. To a 25 mL round-bottomed flask equipped with a magnetic stir bar Then, the reaction mixture was concentrated de vacuo purified via silica gel column chromatography (100% dichloromethane to 1:40 methanol:dichloromethane)

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

Procedure: Hydroquinone (55 g) was dissolved in a solution of sodium hydroxide (20 g) in water (300 ml) and to the resulting solution was added dropwise a solution of tetradecanoyl chloride (123 g) in tetrahydrofuran (150 ml) with cooling. The precipitate formed was filtered off and the filtrate was extracted with ethyl acetate. The extract was thoroughly washed with water to remove unreacted hydroquinone and the solvent was removed. The residue was recrystallized from n-hexane to give hydroquinone monomyristate (20 g). m.p. 75°-78° C. with cooling The precipitate formed was filtered off the filtrate was extracted with ethyl acetate The extract was thoroughly washed with water to remove unreacted hydroquinone the solvent was removed The residue was recrystallized from n-hexane

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

Procedure: A solution of 2.14 (0.024 g, 0.1 mmol) in CH2Cl2 (5 mL) was stirred with pyridine (0.032 mL, 0.4 mmol), a catalytic amount of dimethylaminopyridine, and tetradecanoyl chloride (0.054 mL, 0.2 mmol) for 2 h at room temperature. The solution was concentrated and the residue was purified by flash column chromatography over silica gel with hexane:EtOAc (2:1) as eluant to give 2.15 (0.041 g, 92%) as an oil; [α]22D +1.43° (c 4.2, CHCl3); IR (neat) 1783 and 1743 cm-1 (C=O); 1H NMR (CDCl3) δ 0.85 (distorted triplet, 3 H, CH3), 1.10-1.40 (m, 20 H, CH3 (CH2)10CH2CH2CO), 1.60 (br m, 2 H, CH3 (CH2)10CH2CH2CO), 2.00-2.30 (m, 2 H, H-4), 2.30 (t, J=7.5 Hz, 2 H, CH3 (CH2)10CH2CH2CO), 2.50-2.75 (m, 2 H, H-3), 3.60 (br s, 2 H, CH2OCH2Ph), 4.20 (AB q, J=11.9 Hz, 2 H, CH2OCO), 4.55 (br s, 2 H, CH2OCH2Ph), 7.20-7.40 (m, 5 H, Ph); 13C NMR (CDCl3) δ 14.09, 22.65, 24.81, 26.40, 28.78, 29.07, 29.20, 29.32, 29.42, 29.57, 29.61, 29.64, 31.89, 34.03, 65.99, 72.21, 73.76, 84.94, 127.63, 127.93, 128.49, 137.33, 173.14, 176.30. Anal. Calcd for C27H42O5 : C, 72.61; H, 9.48. Found: C, 72.70; H, 9.50. The solution was concentrated the residue was purified by flash column chromatography over silica gel with hexane:EtOAc (2:1) as eluant

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

Procedure: A solution of 8b (0.2 g, 1.4 mmol) in CH2Cl2 (20 mL) was treated with pyridine (0.45 mL, 5.6 mmol), dimethylaminopyridine (0.034 g, 0.28 mmol), and tetradecanoyl chloride (0.76 mL, 2.8 mmol). After stirring for 2 h at room temperature, the reaction mixture was concentrated, and residue was purified by flash column chromatography over silica gel with hexane:EtOAc (3:1) as eluant to give 8c (0.49 g, 99%) as an oil: IR (neat) 1788 and 1741 cm-1 (C=O); 1H NMR (CDCl3) δ 0.86 (distorted t, 3 H, CH3), 1.25 (m, 20 H, CH3 (CH2)10CH2CH2CO), 1.60 (m, 2 H, CH3 (CH2)10CH2CH2CO), 2.31 (t, J=7.4 Hz, 2 H, CH3 (CH2)10CH2CH2CO), 2.60 (s, 2 H, H-3), 4.12 (AB q, J=11.3 Hz, 2 H, CH2OCOC13H27), 4.20 (AB q, J=9.3 Hz, 2 H, H-5), 5.19 (d, J=17.6 Hz, 1 H, CH=CHH), 5.28 (d, J=10.9 Hz, 1 H, CH=CHH), 5.84 (dd, J=10.9, 17.6 Hz, CH=CH2), 13C NMR (CDCl3) δ 14.02, 22.58, 24.69, 28.99, 29.11, 29.24, 29.34, 29.48, 29.53, 29.56, 31.81, 33.93, 36.57, 45.76, 66.63, 73.60, 116.63, 136.81, 173.27, 175.03. Anal. Calcd for C21H36O4 : C, 71.55; H: 10.30. Found. C, 71.46; H, 10.30. the reaction mixture was concentrated residue was purified by flash column chromatography over silica gel with hexane:EtOAc (3:1) as eluant

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

Procedure: 2.0 g. (0.0196 moles) of 3-dimethylaminopropylamine in 40 ml chloroform was added dropwise to an ice cold chloroform solution (50 ml) of myristoyl chloride (4.17 g., 0.0169 moles). After addition, the ice bath was removed and the solution was stirred for 2 hours. A 25 ml aqueous sodium bicarbonate solution was added and stirred for 30 minutes. The organic layer was then washed with 30 ml aqueous sodium bicarbonate/sodium chloride solution and dried with magnesium sulfate. The solution was concentrated in vacuo and the amide was recrystallized in ethyl acetate to yield 3.29 g. (0.0105 moles, 62.3%) of the subject compound. After addition the ice bath was removed A 25 ml aqueous sodium bicarbonate solution was added stirred for 30 minutes The organic layer was then washed with 30 ml aqueous sodium bicarbonate/sodium chloride solution dried with magnesium sulfate The solution was concentrated in vacuo the amide was recrystallized in ethyl acetate to yield 3.29 g

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

Procedure: 2.0 g. (0.0196 moles) of 3-dimethylaminopropylamine in 40 ml chloroform was added dropwise to an ice cold chloroform solution (50 ml) of myristoyl chloride (4.17 g., 0.0169 moles). After addition, the ice bath was removed and the solution was stirred for 2 hours. A 25 ml aqueous sodium bicarbonate solution was added and stirred for 30 minutes. The organic layer was then washed with 30 ml aqueous sodium bicarbonate/sodium chloride solution and dried with magnesium sulfate. The solution was concentrated in vacuo and the amide was recrystallized in ethyl acetate to yield 3.29 g. (0.0105 moles, 62.3%) of the subject compound. After addition the ice bath was removed A 25 ml aqueous sodium bicarbonate solution was added stirred for 30 minutes The organic layer was then washed with 30 ml aqueous sodium bicarbonate/sodium chloride solution dried with magnesium sulfate The solution was concentrated in vacuo the amide was recrystallized in ethyl acetate to yield 3.29 g

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

Procedure: To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 1.22 ml (4.96 mmol) of myristoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain the powder which was washed with hexane and dried to obtain 1.17 g of the desired compound (74.5%, colorless powder), mp: 80.0°-81.0° C. cooling the mixture was stirred at room temperature for 30 minutes The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water dried The solvent was distilled off The residue was purified by column chromatography (eluent: ethyl acetate) to obtain the powder which was washed with hexane dried

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

Procedure: To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 1.22 ml (4.96 mmol) of myristoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain the powder which was washed with hexane and dried to obtain 1.17 g of the desired compound (74.5%, colorless powder), mp: 80.0°-81.0° C. cooling the mixture was stirred at room temperature for 30 minutes The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water dried The solvent was distilled off The residue was purified by column chromatography (eluent: ethyl acetate) to obtain the powder which was washed with hexane dried

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

Procedure: To a solution of 5.6 g of N-[3(R,S)-hydroxytetradecanoyloxy]succinimide in 150 ml pyridine cooled to 0° are added 4.9 g of tetradecanoylchloride and the reaction mixture maintained at 4° for 12 hours. Excess reagent is destroyed with water, the mixture concentrated by evaporation and the residue chromatographed over silica gel (toluene/ethylacetate=95/5) to obtained the title compound as a syrup. the reaction mixture maintained at 4° for 12 hours Excess reagent is destroyed with water the mixture concentrated by evaporation the residue chromatographed over silica gel (toluene/ethylacetate=95/5)