3-methylbutanethioamide

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isovalerothioamide (6.0 g, 51 mmol) and ethyl formylchloroacetate (Heterocycles 32 (4), 693–701, (1991), 5.0 g, 33 mmol) are dissolved in dry DMF (20 mL), and heated to 95 degrees C. for 4 hours. The reaction is subsequently cooled to 0 degrees C., and cold water (50 mL) is added. The mixture is basified to pH=8 with solid sodium bicarbonate, then extracted with ether (3×35 mL). The combined organic extracts are washed with water, then saline and dried over magnesium sulfate, filtered, and concentrated. The residue is purified by flash chromatography (ethyl acetate/hexanes 4–10% elution) to give the desired product. NMR (CDCl3, 300 MHz) δ 8.27, 4.45–4.30, 3.70–3.50, 3.00–2.80, 2.30–2.10, 1.40–1.20, and 1.10–0.90. The reaction is subsequently cooled to 0 degrees C extracted with ether (3×35 mL) The combined organic extracts are washed with water saline and dried over magnesium sulfate filtered concentrated The residue is purified by flash chromatography (ethyl acetate/hexanes 4–10% elution)

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

Procedure: To a solution of 3-methylbutanethioamide (example 72, step b) (5.6 g) in ethanol (100 mL) was added ethyl 3-bromo-2-oxopropanoate (6.7 mL). The resulting mixture was stirred overnight at RT, then heated at reflux for 5 h. The solvent was evaporated and the residue was partitioned between ethyl acetate (250 mL) and saturated sodium hydrogen carbonate solution (100 mL). The layers were separated and the organic phase was washed with brine (100 mL), dried over magnesium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 20:1 to 10:1 isohexane:ethyl acetate gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 5.2 g. heated at reflux for 5 h The solvent was evaporated the residue was partitioned between ethyl acetate (250 mL) and saturated sodium hydrogen carbonate solution (100 mL) The layers were separated the organic phase was washed with brine (100 mL) dried over magnesium sulphate filtered evaporated The residue was purified by silica gel chromatography eluting with 20:1 to 10:1 isohexane The fractions containing product evaporated

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

Procedure: To a solution of 3-methylbutanethioamide (example 72, step b) (5.6 g) in ethanol (100 mL) was added ethyl 3-bromo-2-oxopropanoate (6.7 mL). The resulting mixture was stirred overnight at RT, then heated at reflux for 5 h. The solvent was evaporated and the residue was partitioned between ethyl acetate (250 mL) and saturated sodium hydrogen carbonate solution (100 mL). The layers were separated and the organic phase was washed with brine (100 mL), dried over magnesium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 20:1 to 10:1 isohexane:ethyl acetate gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 5.2 g. heated at reflux for 5 h The solvent was evaporated the residue was partitioned between ethyl acetate (250 mL) and saturated sodium hydrogen carbonate solution (100 mL) The layers were separated the organic phase was washed with brine (100 mL) dried over magnesium sulphate filtered evaporated The residue was purified by silica gel chromatography eluting with 20:1 to 10:1 isohexane The fractions containing product evaporated

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isovalerothioamide (6.0 g, 51 mmol) and ethyl formylchloroacetate (Heterocycles 32 (4), 693–701, (1991), 5.0 g, 33 mmol) are dissolved in dry DMF (20 mL), and heated to 95 degrees C. for 4 hours. The reaction is subsequently cooled to 0 degrees C., and cold water (50 mL) is added. The mixture is basified to pH=8 with solid sodium bicarbonate, then extracted with ether (3×35 mL). The combined organic extracts are washed with water, then saline and dried over magnesium sulfate, filtered, and concentrated. The residue is purified by flash chromatography (ethyl acetate/hexanes 4–10% elution) to give the desired product. NMR (CDCl3, 300 MHz) δ 8.27, 4.45–4.30, 3.70–3.50, 3.00–2.80, 2.30–2.10, 1.40–1.20, and 1.10–0.90. The reaction is subsequently cooled to 0 degrees C extracted with ether (3×35 mL) The combined organic extracts are washed with water saline and dried over magnesium sulfate filtered concentrated The residue is purified by flash chromatography (ethyl acetate/hexanes 4–10% elution)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isovalerothioamide (6.0 g, 51 mmol) and ethyl formylchloroacetate (Heterocycles 32 (4), 693–701, (1991), 5.0 g, 33 mmol) are dissolved in dry DMF (20 mL), and heated to 95 degrees C. for 4 hours. The reaction is subsequently cooled to 0 degrees C., and cold water (50 mL) is added. The mixture is basified to pH=8 with solid sodium bicarbonate, then extracted with ether (3×35 mL). The combined organic extracts are washed with water, then saline and dried over magnesium sulfate, filtered, and concentrated. The residue is purified by flash chromatography (ethyl acetate/hexanes 4–10% elution) to give the desired product. NMR (CDCl3, 300 MHz) δ 8.27, 4.45–4.30, 3.70–3.50, 3.00–2.80, 2.30–2.10, 1.40–1.20, and 1.10–0.90. The reaction is subsequently cooled to 0 degrees C extracted with ether (3×35 mL) The combined organic extracts are washed with water saline and dried over magnesium sulfate filtered concentrated The residue is purified by flash chromatography (ethyl acetate/hexanes 4–10% elution)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isovalerothioamide (6.0 g, 51 mmol) and ethyl formylchloroacetate (Heterocycles 32 (4), 693-701, (1991), 5.0 g, 33 mmol) are dissolved in dry DMF (20 mL), and heated to 95 degrees C. for 4 hours. The reaction is subsequently cooled to 0 degrees C., and cold water (50 mL) is added. The mixture is basified to pH=8 with solid sodium bicarbonate, then extracted with ether (3×35 mL). The combined organic extracts are washed with water, then saline and dried over magnesium sulfate, filtered, and concentrated. The residue is purified by flash chromatography (ethyl acetate/hexanes 4-10% elution) to give the desired product. NMR (CDCl3, 300 MHz) δ 8.27, 4.45-4.30, 3.70-3.50, 3.00-2.80, 2.30-2.10, 1.40-1.20, and 1.10-0.90. The reaction is subsequently cooled to 0 degrees C extracted with ether (3×35 mL) The combined organic extracts are washed with water saline and dried over magnesium sulfate filtered concentrated The residue is purified by flash chromatography (ethyl acetate/hexanes 4-10% elution)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isovalerothioamide (6.0 g, 51 mmol) and ethyl formylchloroacetate (Heterocycles 32 (4), 693-701, (1991), 5.0 g, 33 mmol) are dissolved in dry DMF (20 mL), and heated to 95 degrees C. for 4 hours. The reaction is subsequently cooled to 0 degrees C., and cold water (50 mL) is added. The mixture is basified to pH=8 with solid sodium bicarbonate, then extracted with ether (3×35 mL). The combined organic extracts are washed with water, then saline and dried over magnesium sulfate, filtered, and concentrated. The residue is purified by flash chromatography (ethyl acetate/hexanes 4-10% elution) to give the desired product. NMR (CDCl3, 300 MHz) δ 8.27, 4.45-4.30, 3.70-3.50, 3.00-2.80, 2.30-2.10, 1.40-1.20, and 1.10-0.90. The reaction is subsequently cooled to 0 degrees C extracted with ether (3×35 mL) The combined organic extracts are washed with water saline and dried over magnesium sulfate filtered concentrated The residue is purified by flash chromatography (ethyl acetate/hexanes 4-10% elution)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isovalerothioamide (6.0 g, 51 mmol) and ethyl formylchloroacetate (Heterocycles 32 (4), 693-701, (1991), 5.0 g, 33 mmol) are dissolved in dry DMF (20 mL), and heated to 95 degrees C. for 4 hours. The reaction is subsequently cooled to 0 degrees C., and cold water (50 mL) is added. The mixture is basified to pH=8 with solid sodium bicarbonate, then extracted with ether (3×35 mL). The combined organic extracts are washed with water, then saline and dried over magnesium sulfate, filtered, and concentrated. The residue is purified by flash chromatography (ethyl acetate/hexanes 4-10% elution) to give the desired product. NMR (CDCl3, 300 MHz) δ 8.27, 4.45-4.30, 3.70-3.50, 3.00-2.80, 2.30-2.10, 1.40-1.20, and 1.10-0.90. The reaction is subsequently cooled to 0 degrees C extracted with ether (3×35 mL) The combined organic extracts are washed with water saline and dried over magnesium sulfate filtered concentrated The residue is purified by flash chromatography (ethyl acetate/hexanes 4-10% elution)

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

Procedure: To a solution of 3-methylbutanethioamide (example 72, step b) (5.6 g) in ethanol (100 mL) was added ethyl 3-bromo-2-oxopropanoate (6.7 mL). The resulting mixture was stirred overnight at RT, then heated at reflux for 5 h. The solvent was evaporated and the residue was partitioned between ethyl acetate (250 mL) and saturated sodium hydrogen carbonate solution (100 mL). The layers were separated and the organic phase was washed with brine (100 mL), dried over magnesium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 20:1 to 10:1 isohexane:ethyl acetate gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 5.2 g. heated at reflux for 5 h The solvent was evaporated the residue was partitioned between ethyl acetate (250 mL) and saturated sodium hydrogen carbonate solution (100 mL) The layers were separated the organic phase was washed with brine (100 mL) dried over magnesium sulphate filtered evaporated The residue was purified by silica gel chromatography eluting with 20:1 to 10:1 isohexane The fractions containing product evaporated

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isovalerothioamide (6.0 g, 51 mmol) and ethyl formylchloroacetate (Heterocycles 32 (4), 693–701, (1991), 5.0 g, 33 mmol) are dissolved in dry DMF (20 mL), and heated to 95 degrees C. for 4 hours. The reaction is subsequently cooled to 0 degrees C., and cold water (50 mL) is added. The mixture is basified to pH=8 with solid sodium bicarbonate, then extracted with ether (3×35 mL). The combined organic extracts are washed with water, then saline and dried over magnesium sulfate, filtered, and concentrated. The residue is purified by flash chromatography (ethyl acetate/hexanes 4–10% elution) to give the desired product. NMR (CDCl3, 300 MHz) δ 8.27, 4.45–4.30, 3.70–3.50, 3.00–2.80, 2.30–2.10, 1.40–1.20, and 1.10–0.90. The reaction is subsequently cooled to 0 degrees C extracted with ether (3×35 mL) The combined organic extracts are washed with water saline and dried over magnesium sulfate filtered concentrated The residue is purified by flash chromatography (ethyl acetate/hexanes 4–10% elution)

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

Procedure: To a solution of 3-methylbutanethioamide (example 72, step b) (5.6 g) in ethanol (100 mL) was added ethyl 3-bromo-2-oxopropanoate (6.7 mL). The resulting mixture was stirred overnight at RT, then heated at reflux for 5 h. The solvent was evaporated and the residue was partitioned between ethyl acetate (250 mL) and saturated sodium hydrogen carbonate solution (100 mL). The layers were separated and the organic phase was washed with brine (100 mL), dried over magnesium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 20:1 to 10:1 isohexane:ethyl acetate gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 5.2 g. heated at reflux for 5 h The solvent was evaporated the residue was partitioned between ethyl acetate (250 mL) and saturated sodium hydrogen carbonate solution (100 mL) The layers were separated the organic phase was washed with brine (100 mL) dried over magnesium sulphate filtered evaporated The residue was purified by silica gel chromatography eluting with 20:1 to 10:1 isohexane The fractions containing product evaporated

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isovalerothioamide (6.0 g, 51 mmol) and ethyl formylchloroacetate (Heterocycles 32 (4), 693–701, (1991), 5.0 g, 33 mmol) are dissolved in dry DMF (20 mL), and heated to 95 degrees C. for 4 hours. The reaction is subsequently cooled to 0 degrees C., and cold water (50 mL) is added. The mixture is basified to pH=8 with solid sodium bicarbonate, then extracted with ether (3×35 mL). The combined organic extracts are washed with water, then saline and dried over magnesium sulfate, filtered, and concentrated. The residue is purified by flash chromatography (ethyl acetate/hexanes 4–10% elution) to give the desired product. NMR (CDCl3, 300 MHz) δ 8.27, 4.45–4.30, 3.70–3.50, 3.00–2.80, 2.30–2.10, 1.40–1.20, and 1.10–0.90. The reaction is subsequently cooled to 0 degrees C extracted with ether (3×35 mL) The combined organic extracts are washed with water saline and dried over magnesium sulfate filtered concentrated The residue is purified by flash chromatography (ethyl acetate/hexanes 4–10% elution)