Methyl isothiocyanate → 2-Hydroxy-5-methyl-3-[[6-[[(methylamino) thioxomethyl]amino]-2-[[3-(1-naphthalenyl)-2-(1-naphthalenylmethyl)-1-oxopropyl]amino]-1-oxohexyl]amino]hexanoicacid, 1-methylethyl ester

Participants

Reaction Steps

[2R-[2R*,3S*(S*)]]-3-[[6-amino-2-[[3-(1-naphthalenyl)-2-(1-naphthalenylmethyl)-1-oxopropyl]amino]-1-oxohexyl]amino]-2-hydroxy-5-methylhexanoic acid, 1-methylethyl ester (Example K), 3.44 g (5.3 mmol), is dissolved in 65 ml of chloroform, 0.42 g (5.7 mmol) of methyl isothiocyanate is added, and the reaction mixture is stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture is concentrated and 2.05 g (53% yield) of the title compound is obtained after flash chromatography over silica gel 60 (230-400 mesh) and elution with hexane-ethyl acetate (1:4); mp softens at 89° C., melts at 93°-95° C.

Provenance & Evidence