Triethylamine → n-((5s)-3-(4-(1-Cyano-2s-(pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

Participants

Reaction Steps

The amine (Reference Example 7, 0.103 g, 0.24 mM) in CH2Cl2 (4 ml) was treated with triethylamine (0.073 g, 0.100 ml, 0.72 mM) and 4-dimethylaminopyridine (4-DMAP) (0.003 g, 0.024 mM), followed by a suspension of cyanogen bromide (0.129 g, 1.21 mM) in CH2Cl2 (3 ml). The solution was stirred for 1 hour. The mixture was then diluted with CH2Cl2 (7 ml), washed with sat. aq. NaHCO3 (3 ml), water (3 ml), dried and evaporated to an oil which was purified by Isolute chromatography (using as eluant 6% MeOH/CH2Cl2). The resultant oil was triturated with diethyl ether to give the title product (0.071 g, 66%).

Provenance & Evidence