(2S)-2-amino-4-methylsulfanylbutanamide

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5.78 g (0.039 mole) of H-Met-NH2 was dissolved in 50 ml of DMF, then 5.46 ml of triethylamine and further 18.70 g (0.047 mole) of Boc-Trp-OSu were added under cooling with ice, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, and extracted with ethyl acetate. The extract was washed with 1N citric acid, saturated saline solution, saturated sodium bicarbonate solution, and saturated saline solution in series. The resulting organic layer was dried over anhydrous sodium sulfate, distilled in vacuo to remove the solvent, and solidified with hexane. The solid was recrystallized from ethyl acetate-hexane, giving 12.45 g of Boc-Trp-Met-NH2 ; yield 73.5%, m.p. 155°-157° C. under cooling with ice The reaction mixture was concentrated in vacuo extracted with ethyl acetate The extract was washed with 1N citric acid, saturated saline solution, saturated sodium bicarbonate solution, and saturated saline solution in series The resulting organic layer was dried over anhydrous sodium sulfate distilled in vacuo to remove the solvent The solid was recrystallized from ethyl acetate-hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-(Benzylsulfonyl)-D-isoleucyl-N1-(4-cyanobenzyl)-L-methioninamide (100 mg, 0.19 mmol) was dissolved in ethanol (6 ml) and pyridine (0.6 ml), to which hydroxyamine hydrochloride (120 mg) was then added and stirred for 16 hours. After the solvent was distilled off under reduced pressure, the residue was dissolved in ethanol, filtered and then purified by preparative HPLC to give N-(benzylsulfonyl)-D-isoleucyl-N1-[4-(E)-amino(hydroxyimino)methyl]benzyl]-L-methioninamide (1.6 mg, 0.00003 mmol; yield 1.5%). After the solvent was distilled off under reduced pressure the residue was dissolved in ethanol filtered purified by preparative HPLC

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-(Benzylsulfonyl)-D-isoleucyl-N1-(4-cyanobenzyl)-L-methioninamide (100 mg, 0.19 mmol) was dissolved in ethanol (6 ml) and pyridine (0.6 ml), to which hydroxyamine hydrochloride (120 mg) was then added and stirred for 16 hours. After the solvent was distilled off under reduced pressure, the residue was dissolved in ethanol, filtered and then purified by preparative HPLC to give N-(benzylsulfonyl)-D-isoleucyl-N1-[4-(E)-amino(hydroxyimino)methyl]benzyl]-L-methioninamide (1.6 mg, 0.00003 mmol; yield 1.5%). After the solvent was distilled off under reduced pressure the residue was dissolved in ethanol filtered purified by preparative HPLC

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5.78 g (0.039 mole) of H-Met-NH2 was dissolved in 50 ml of DMF, then 5.46 ml of triethylamine and further 18.70 g (0.047 mole) of Boc-Trp-OSu were added under cooling with ice, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, and extracted with ethyl acetate. The extract was washed with 1N citric acid, saturated saline solution, saturated sodium bicarbonate solution, and saturated saline solution in series. The resulting organic layer was dried over anhydrous sodium sulfate, distilled in vacuo to remove the solvent, and solidified with hexane. The solid was recrystallized from ethyl acetate-hexane, giving 12.45 g of Boc-Trp-Met-NH2 ; yield 73.5%, m.p. 155°-157° C. under cooling with ice The reaction mixture was concentrated in vacuo extracted with ethyl acetate The extract was washed with 1N citric acid, saturated saline solution, saturated sodium bicarbonate solution, and saturated saline solution in series The resulting organic layer was dried over anhydrous sodium sulfate distilled in vacuo to remove the solvent The solid was recrystallized from ethyl acetate-hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5.78 g (0.039 mole) of H-Met-NH2 was dissolved in 50 ml of DMF, then 5.46 ml of triethylamine and further 18.70 g (0.047 mole) of Boc-Trp-OSu were added under cooling with ice, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, and extracted with ethyl acetate. The extract was washed with 1N citric acid, saturated saline solution, saturated sodium bicarbonate solution, and saturated saline solution in series. The resulting organic layer was dried over anhydrous sodium sulfate, distilled in vacuo to remove the solvent, and solidified with hexane. The solid was recrystallized from ethyl acetate-hexane, giving 12.45 g of Boc-Trp-Met-NH2 ; yield 73.5%, m.p. 155°-157° C. under cooling with ice The reaction mixture was concentrated in vacuo extracted with ethyl acetate The extract was washed with 1N citric acid, saturated saline solution, saturated sodium bicarbonate solution, and saturated saline solution in series The resulting organic layer was dried over anhydrous sodium sulfate distilled in vacuo to remove the solvent The solid was recrystallized from ethyl acetate-hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-(Benzylsulfonyl)-D-isoleucyl-N1-(4-cyanobenzyl)-L-methioninamide (100 mg, 0.19 mmol) was dissolved in ethanol (6 ml) and pyridine (0.6 ml), to which hydroxyamine hydrochloride (120 mg) was then added and stirred for 16 hours. After the solvent was distilled off under reduced pressure, the residue was dissolved in ethanol, filtered and then purified by preparative HPLC to give N-(benzylsulfonyl)-D-isoleucyl-N1-[4-(E)-amino(hydroxyimino)methyl]benzyl]-L-methioninamide (1.6 mg, 0.00003 mmol; yield 1.5%). After the solvent was distilled off under reduced pressure the residue was dissolved in ethanol filtered purified by preparative HPLC

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5.78 g (0.039 mole) of H-Met-NH2 was dissolved in 50 ml of DMF, then 5.46 ml of triethylamine and further 18.70 g (0.047 mole) of Boc-Trp-OSu were added under cooling with ice, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, and extracted with ethyl acetate. The extract was washed with 1N citric acid, saturated saline solution, saturated sodium bicarbonate solution, and saturated saline solution in series. The resulting organic layer was dried over anhydrous sodium sulfate, distilled in vacuo to remove the solvent, and solidified with hexane. The solid was recrystallized from ethyl acetate-hexane, giving 12.45 g of Boc-Trp-Met-NH2 ; yield 73.5%, m.p. 155°-157° C. under cooling with ice The reaction mixture was concentrated in vacuo extracted with ethyl acetate The extract was washed with 1N citric acid, saturated saline solution, saturated sodium bicarbonate solution, and saturated saline solution in series The resulting organic layer was dried over anhydrous sodium sulfate distilled in vacuo to remove the solvent The solid was recrystallized from ethyl acetate-hexane