4-(4-methylphenyl)butanoyl chloride

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-dimethylaminopyridine (1.17 g, 11.8 mmol) and 4-(4-methylphenyl)butyric chloride (1.06 g, 5.90 mmol) in toluene (5 mL) was added to a solution of (2R)-1-acetoxy-2-acetylamino-2-ethyl-4-(1-methylpyrrol-2-yl)butane (444 mg, 1.60 mmol) obtained in Reference example 2 in toluene (15 mL) and the mixture was stirred at 110° C. for 72 hours. The temperature of the mixture was returned to room temperature and ethyl acetate and water were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with water and a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1) to obtain the title compound (377 mg, yield: 40%). was returned to room temperature to separate it The thus obtained organic phase was separated washed with water a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate After filtration the solvent was evaporated under reduced pressure the residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1)

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-dimethylaminopyridine (1.17 g, 11.8 mmol) and 4-(4-methylphenyl)butyric chloride (1.06 g, 5.90 mmol) in toluene (5 mL) was added to a solution of (2R)-1-acetoxy-2-acetylamino-2-ethyl-4-(1-methylpyrrol-2-yl)butane (444 mg, 1.60 mmol) obtained in Reference example 2 in toluene (15 mL) and the mixture was stirred at 110° C. for 72 hours. The temperature of the mixture was returned to room temperature and ethyl acetate and water were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with water and a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1) to obtain the title compound (377 mg, yield: 40%). was returned to room temperature to separate it The thus obtained organic phase was separated washed with water a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate After filtration the solvent was evaporated under reduced pressure the residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1)

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thionyl chloride (9.0 mL, 123 mmol) and N,N -dimethylformamide (50 μL) were added to a solution of 4-(4-methylphenyl)butyric acid (11.0 g, 62.0 mmol) in benzene (220 mL) and the mixture was stirred at 80° C. for 2 hours. After cooling the mixture to room temperature, the solvent was evaporated under reduced pressure to obtain 5-(4-methylphenyl)butyric chloride. A solution of 4-dimethylaminopyridine (15.2 g, 124 mmol) and 4-(4-methylphenyl)butyric chloride (12.2 g, 62.0 mmol) in toluene (50 mL) was added to a solution of (2R)-1-acetoxy-2-acetylamino-2-methyl-4-(1-methylpyrrol-2-yl)butane (5.00 g, 18.8 mmol) obtained in Reference example 1 in toluene (150 mL) and the mixture was stirred at 110° C. for 48 hours. The temperature of the mixture was returned to room temperature and ethyl acetate and water were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with water and a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1) to obtain the title compound (5.15 g, yield: 47%). was returned to room temperature to separate it The thus obtained organic phase was separated washed with water a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1)

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-dimethylaminopyridine (1.17 g, 11.8 mmol) and 4-(4-methylphenyl)butyric chloride (1.06 g, 5.90 mmol) in toluene (5 mL) was added to a solution of (2R)-1-acetoxy-2-acetylamino-2-ethyl-4-(1-methylpyrrol-2-yl)butane (444 mg, 1.60 mmol) obtained in Reference example 2 in toluene (15 mL) and the mixture was stirred at 110° C. for 72 hours. The temperature of the mixture was returned to room temperature and ethyl acetate and water were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with water and a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1) to obtain the title compound (377 mg, yield: 40%). was returned to room temperature to separate it The thus obtained organic phase was separated washed with water a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate After filtration the solvent was evaporated under reduced pressure the residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1)

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thionyl chloride (9.0 mL, 123 mmol) and N,N -dimethylformamide (50 μL) were added to a solution of 4-(4-methylphenyl)butyric acid (11.0 g, 62.0 mmol) in benzene (220 mL) and the mixture was stirred at 80° C. for 2 hours. After cooling the mixture to room temperature, the solvent was evaporated under reduced pressure to obtain 5-(4-methylphenyl)butyric chloride. A solution of 4-dimethylaminopyridine (15.2 g, 124 mmol) and 4-(4-methylphenyl)butyric chloride (12.2 g, 62.0 mmol) in toluene (50 mL) was added to a solution of (2R)-1-acetoxy-2-acetylamino-2-methyl-4-(1-methylpyrrol-2-yl)butane (5.00 g, 18.8 mmol) obtained in Reference example 1 in toluene (150 mL) and the mixture was stirred at 110° C. for 48 hours. The temperature of the mixture was returned to room temperature and ethyl acetate and water were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with water and a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1) to obtain the title compound (5.15 g, yield: 47%). was returned to room temperature to separate it The thus obtained organic phase was separated washed with water a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1)