(2S)-6-[[(2S)-3-(1H-indol-3-yl)-2-[(4-nitrophenyl)sulfonylamino]propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid → (2S)-6-[[(2S)-2-[(4-aminophenyl)sulfonylamino]-3-(1H-indol-3-yl)propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Participants

Reaction Steps

The title compound was prepared from Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine hydrochloride (200 mg, 0.59 mmol, example 1, step E) as described in general procedure Bc using Nα-(4-nitrobenzenesulfonyl)-L-tryptophan (300 mg, 0.75 mmol) prepared in step A of example 5. The intermediate, Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-Nε-[N′α-(4-nitrobenzenesulfonyl)-L-tryptophanyl]-L-lysine, was reduced following the conditions of general procedure E. The final product was purified by preparative HPLC to yield 266 mg (58%) of the desired material.

Provenance & Evidence