undec-10-enoyl 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: Add undec-10-enoyl chloride (2 g.) in benzene (6 cc.) to 13β-ethyl-17β-hydroxy-gon-4-en-3-one (2 g.) in pyridine (6 cc.) at -15°. Keep the mixture at -10° for 17 hours, add to water and extract with benzene. Wash, dryand evaporate the extracts and recrystallize the residue from ethanol to obtain the title compound, m.p. 87°-88°; ultraviolet absorption peak at 240 mμ (ε17,000); infrared absorption peaks at 5.79, 6.00, 6.20 μ. at -10° for 17 hours extract with benzene Wash evaporate the extracts recrystallize the residue from ethanol

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

Procedure: Add undec-10-enoyl chloride (2 g.) in benzene (6 cc.) to 13β-ethyl-17β-hydroxy-gon-4-en-3-one (2 g.) in pyridine (6 cc.) at -15°. Keep the mixture at -10° for 17 hours, add to water and extract with benzene. Wash, dryand evaporate the extracts and recrystallize the residue from ethanol to obtain the title compound, m.p. 87°-88°; ultraviolet absorption peak at 240 mμ (ε17,000); infrared absorption peaks at 5.79, 6.00, 6.20 μ. at -10° for 17 hours extract with benzene Wash evaporate the extracts recrystallize the residue from ethanol

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

Procedure: A 50-mL, one-necked, round-bottomed flask was charged with 10 mL toluene, triethylamine (0.70 mL, 5.0 mmol) and thiophenol (0.51 mL, 5.0 mmol). A solution of 10-undecenoyl chloride (1.10 mL, 5.1 mmol) in 15 mL toluene was added by a pressure-equalizing dropping funnel over 30 min while stirring the solution with a magnetic stirrer. over 30 min

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

Procedure: Employing substantially the same procedure as described in Example 6, but substituting 20-hydroxy-5α-4-azapregn-1-ene-3-one and trimethylacetyl chloride for the 20-hydroxy-4-methyl-5α-4-azapregnan-3-one and 10-undecenoyl chloride, respectively, used therein, the title compound was obtained. MS M-1 calculated for C25H39NO3, mw=402.53; observed m/e 401.

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

Procedure: To a solution of 20-hydroxy-4-methyl-5α-4-azapregnan-3-one (0.167 g, 0.5 mM) and pyridine (0.1 mL) in anhydrous methylene chloride (4.5 mL) at ice-bath temperatures was added 10-undecenoyl chloride (0.13 mL, 0.6 mM) dropwise. After 10 minutes, the reaction mixture was allowed to warm to room temperature and stir overnight. After diluting further with methylene chloride the mixture was washed with dilute hydrochloric acid, water, and brine, and dried (Na2SO4). The residue obtained from concentration of the filtered solution was flash chromatographed on silica gel using ethyl acetate as eluant to give the title compound as a glaze. MS M+ calculated for C32H53NO3, mw=499.78; observed m/e 499. was washed with dilute hydrochloric acid, water, and brine dried (Na2SO4) The residue obtained from concentration of the filtered solution chromatographed on silica gel

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 9-decenyl isocyanate, prepared as in Example 18 above from 10.8 ml of 10-undecenoyl chloride in 1,2-dichloroethane (150 ml) at room temperature was added benzyloxyamine (7.2 g). After 20 minutes, the mixture was evaporated, hexane (50 ml) was added, and the mixture cooled to 0° C. The resulting solids were collected by filtration, to provide N-(9-decenyl)-N'-benzyloxyurea as a white solid (7.14 g, mp 53°-55° C.). To a stirred slurry of this urea (3.50 g, 11.65 mmol) in DMF (35 ml) at room temperature under nitrogen was added sodium hydride (490 mg of a 60% dispersion in oil). After one hour, 1,3-dibromopropane (1.45 ml) was added, and the reaction was stirred for two hours. The mixture was poured into 1% aqueous HCl (200 ml), and extracted twice with ether. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated. Purification by chromatography on silica gave 3-decyl-1-benzyloxy-3,4,5,6-tetrahydro-lH-pyrimidin-2-one as a colorless oil (1.92 g, 48% yield). Hydrogenolysis as in Example 2 above provided the title compound as a light magenta solid, after recrystallization from carbon tetrachloride, mp 45°-46° C. the mixture was evaporated hexane (50 ml) was added The resulting solids were collected by filtration

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

Procedure: To a stirred solution of sodium azide (1.32 g) in water (5 ml) at 0° C. was added a solution of 10-undecenoyl chloride (4.30 ml) in dioxane (10 ml). The mixture was stirred for 45 minutes, and poured into ice water (100 ml). The mixture was extracted twice with benzene (50 ml), and the combined extracts were washed with ice water (25 ml), dried (MgSO4), and filtered. The filtrate was heated to reflux under a Dean-Stark trap, removing the first 30 ml of distillate. After 30 minutes at reflux, the reaction was cooled and evaporated, to provide 9-decenyl icocyanate as a colorless oil. This isocyanate was dissolved in DMF (5 ml) and added to a slurry of N-methylhydroxylamine hydrochloride (1.70 g) and triethylamine (2.84 ml) in DMF (20 ml). After two hours, the reaction mixture was filtered through Celite and quenched with water. The resulting solids were collected by filtration, washed with water, and recrystallized from ethyl acetate to provide the title compound as a white solid (1.35 g), mp 58°-59° C. The mixture was extracted twice with benzene (50 ml) the combined extracts were washed with ice water (25 ml) dried (MgSO4) filtered The filtrate was heated to reflux under a Dean-Stark trap removing the first 30 ml of distillate After 30 minutes at reflux the reaction was cooled evaporated to provide 9-decenyl icocyanate as a colorless oil After two hours the reaction mixture was filtered through Celite quenched with water The resulting solids were collected by filtration washed with water recrystallized from ethyl acetate

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

Procedure: To a stirred solution of sodium azide (1.32 g) in water (5 ml) at 0° C. was added a solution of 10-undecenoyl chloride (4.30 ml) in dioxane (10 ml). The mixture was stirred for 45 minutes, and poured into ice water (100 ml). The mixture was extracted twice with benzene (50 ml), and the combined extracts were washed with ice water (25 ml), dried (MgSO4), and filtered. The filtrate was heated to reflux under a Dean-Stark trap, removing the first 30 ml of distillate. After 30 minutes at reflux, the reaction was cooled and evaporated, to provide 9-decenyl icocyanate as a colorless oil. This isocyanate was dissolved in DMF (5 ml) and added to a slurry of N-methylhydroxylamine hydrochloride (1.70 g) and triethylamine (2.84 ml) in DMF (20 ml). After two hours, the reaction mixture was filtered through Celite and quenched with water. The resulting solids were collected by filtration, washed with water, and recrystallized from ethyl acetate to provide the title compound as a white solid (1.35 g), mp 58°-59° C. The mixture was extracted twice with benzene (50 ml) the combined extracts were washed with ice water (25 ml) dried (MgSO4) filtered The filtrate was heated to reflux under a Dean-Stark trap removing the first 30 ml of distillate After 30 minutes at reflux the reaction was cooled evaporated to provide 9-decenyl icocyanate as a colorless oil After two hours the reaction mixture was filtered through Celite quenched with water The resulting solids were collected by filtration washed with water recrystallized from ethyl acetate