1-Hydroxybenzotriazole → N-(benzyl-sulfonyl)-D-tryptophyl-N1-(4-aminobenzyl)-L-methioninamide

Participants

Reaction Steps

To a solution of N-(benzylsulfonyl)-D-isoleucyl-L-methionine (100 mg, 0.24 mmol) and 4-aminobenzylamine (59 mg, 0.48 mmol) in dichloromethane (5 ml), HOBt (44 mg, 0.29 mmol) and EDC HCl (56 mg, 0.29 mmol) were added and stirred at room temperature under a nitrogen stream. After 12 hours, the reaction mixture was concentrated under reduced pressure and water was added to the residue. The precipitated product was collected by filtration, washed with water and then dried. The resulting crude product was applied to column chromatography (Fuji Silysia NH-DM-1020; mobile phase: dichloromethane:methanol=10:1) to give N-(benzyl-sulfonyl)-D-tryptophyl-N1-(4-aminobenzyl)-L-methioninamide (108 mg, 0.21 mmol; yield 86%).

Provenance & Evidence