L-Tryptophan, N-[(4-methylphenyl)sulfonyl]- → (2S)-2-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-[[(2S)-3-(1H-indol-3-yl)-2-(p-tolylsulfonylamino)propanoyl]amino]hexanoic acid

Participants

Reaction Steps

The title compound was prepared from Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine hydrochloride (350 mg, 1.0 mmol, example 5, step C) as described in general procedure Bc using Nα-(4-methylbenzenesulfonyl)-L-tryptophan (335 mg, 1.1 mmol) which was prepared in step A of example 2. The final product was purified by preparative HPLC to yield 650 mg (90%) of Nα-(4-nitrobenzenesulfonyl)-Nα-isobutyl-Nε-[N′α-(4-methylbenzenesulfonyl)-L-tryptophanyl]-L-lysine. The latter derivative (300 mg) was hydrogenolysed following the indications of general procedure E. Purification by HPLC gave the desired material (235 mg, 75%).

Provenance & Evidence