tert-butyl N-(5-aminopentyl)carbamate

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: A solution of 7.78 g (20 mmol) of 3-[(trimethylammonio)methyl]-5-ethoxycarbonylimidazo[1,2-a]pyridine iodide, 6.07 g (30 mmol) of 5-tert-butoxycarbonylamino-1-pentylamine and 5.58 ml (40 mmol) of triethylamine was heated for 64 hours under reflux. The solvent was distilled off. To the residue was added methylene chloride, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1) to afford 3.93 g of the desired compound (54.9%, a pale yellow solid). under reflux The solvent was distilled off To the residue was added methylene chloride washed with water dried over anhydrous magnesium sulfate The solvent was distilled off the residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1)

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

Procedure: A solution of 7.78 g (20 mmol) of 3-[(trimethylammonio)methyl]-5-ethoxycarbonylimidazo[1,2-a]pyridine iodide, 6.07 g (30 mmol) of 5-tert-butoxycarbonylamino-1-pentylamine and 5.58 ml (40 mmol) of triethylamine was heated for 64 hours under reflux. The solvent was distilled off. To the residue was added methylene chloride, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1) to afford 3.93 g of the desired compound (54.9%, a pale yellow solid). under reflux The solvent was distilled off To the residue was added methylene chloride washed with water dried over anhydrous magnesium sulfate The solvent was distilled off the residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1)

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

Procedure: 4.2 ml (30.1 mmol) of triethylamine is added to a solution of 3.21 g (14.5 mmol) of 3-nitrobenzenesulfonyl chloride and 3.0 ml (14.4 mmol) of N-Boc-1,5-diaminopentane in 50 ml of acetone and 15 ml of water. The reaction mixture is stirred for one hour at room temperature. Then, the acetone is drawn off in a rotary evaporator. After water (20 ml) is added, it is extracted with ethyl acetate (2×). The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. 5.00 g (12.9 mmol, corresponding to 90% of theory) of the product is obtained as a light yellow oil. Then, the acetone is drawn off in a rotary evaporator After water (20 ml) is added it is extracted with ethyl acetate (2×) The combined organic phases are dried (Na2SO4) filtered concentrated by evaporation 5.00 g (12.9 mmol, corresponding to 90% of theory) of the product is obtained as a light yellow oil

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

Procedure: To a stirred solution of 5-(tert-butoxycarbonylamino)pentylamine (1.00 g, 4.94 mmol) and triethylamine (689 μL g, 4.94 mmol) in dichloromethane (22 mL) at 0° C. was added 2-chloro-1-ethanesulfonyl chloride (470 μL, 4.50 mmol). The reaction mixture was stirred for 2 h at room temperature and then washed with saturated aqueous sodium bicarbonate solution (15 mL). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give the title compound (100% yield), which was used in the next step without further purification. washed with saturated aqueous sodium bicarbonate solution (15 mL) The organic layer was dried (Na2SO4) the solvent was removed under reduced pressure

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

Procedure: To a stirred solution of 5-(tert-butoxycarbonylamino)pentylamine (1.00 g, 4.94 mmol) and triethylamine (689 μL g, 4.94 mmol) in dichloromethane (22 mL) at 0° C. was added 2-chloro-1-ethanesulfonyl chloride (470 μL, 4.50 mmol). The reaction mixture was stirred for 2 h at room temperature and then washed with saturated aqueous sodium bicarbonate solution (15 mL). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give the title compound (100% yield), which was used in the next step without further purification. washed with saturated aqueous sodium bicarbonate solution (15 mL) The organic layer was dried (Na2SO4) the solvent was removed under reduced pressure

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

Procedure: To a stirred solution of 5-(tert-butoxycarbonylamino)pentylamine (1.00 g, 4.94 mmol) and triethylamine (689 μL g, 4.94 mmol) in dichloromethane (22 mL) at 0° C. was added 2-chloro-1-ethanesulfonyl chloride (470 μL, 4.50 mmol). The reaction mixture was stirred for 2 h at room temperature and then washed with saturated aqueous sodium bicarbonate solution (15 mL). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give the title compound (100% yield), which was used in the next step without further purification. washed with saturated aqueous sodium bicarbonate solution (15 mL) The organic layer was dried (Na2SO4) the solvent was removed under reduced pressure

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

Procedure: To a stirred solution of 5-(tert-butoxycarbonylamino)pentylamine (1.00 g, 4.94 mmol) and triethylamine (689 μL g, 4.94 mmol) in dichloromethane (22 mL) at 0° C. was added 2-chloro-1-ethanesulfonyl chloride (470 μL, 4.50 mmol). The reaction mixture was stirred for 2 h at room temperature and then washed with saturated aqueous sodium bicarbonate solution (15 mL). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give the title compound (100% yield), which was used in the next step without further purification. washed with saturated aqueous sodium bicarbonate solution (15 mL) The organic layer was dried (Na2SO4) the solvent was removed under reduced pressure

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

Procedure: To a stirred solution of 5-(tert-butoxycarbonylamino)pentylamine (1.00 g, 4.94 mmol) and triethylamine (689 μL g, 4.94 mmol) in dichloromethane (22 mL) at 0° C. was added 2-chloro-1-ethanesulfonyl chloride (470 μL, 4.50 mmol). The reaction mixture was stirred for 2 h at room temperature and then washed with saturated aqueous sodium bicarbonate solution (15 mL). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give the title compound (100% yield), which was used in the next step without further purification. washed with saturated aqueous sodium bicarbonate solution (15 mL) The organic layer was dried (Na2SO4) the solvent was removed under reduced pressure

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

Procedure: To a stirred solution of 5-(tert-butoxycarbonylamino)pentylamine (1.00 g, 4.94 mmol) and triethylamine (689 μL, g, 4.94 mmol) in dichloromethane (22 mL) at 0° C. was added 2-chloro-1-ethanesulfonyl chloride (470 μL, 4.50 mmol). The reaction mixture was stirred for 2 h at room temperature and then washed with saturated aqueous sodium bicarbonate solution (15 mL). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give the title compound (100% yield), which was used in the next step without further purification. washed with saturated aqueous sodium bicarbonate solution (15 mL) The organic layer was dried (Na2SO4) the solvent was removed under reduced pressure

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

Procedure: To a stirred solution of 5-(tert-butoxycarbonylamino)pentylamine (1.00 g, 4.94 mmol) and triethylamine (689 μL g, 4.94 mmol) in dichloromethane (22 mL) at 0° C. was added 2-chloro-1-ethanesulfonyl chloride (470 μL, 4.50 mmol). The reaction mixture was stirred for 2 h at room temperature and then washed with saturated aqueous sodium bicarbonate solution (15 mL). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give the title compound (100% yield), which was used in the next step without further purification. washed with saturated aqueous sodium bicarbonate solution (15 mL) The organic layer was dried (Na2SO4) the solvent was removed under reduced pressure