4-Methylmorpholine → (R)-3-{4-[4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-methyloxazolidin-2-one hydrochloride

Participants

Reaction Steps

(R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid (442 mg) described in Preparation Example 37, 1-(3-cyclopropyl-5-methylpyridin-2-yl)piperazine hydrochloride (435 mg) described in Preparation Example 48 and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (829 mg) were dissolved in chloroform (3 mL) and methanol (3 mL), N-methylmorpholine (220 μL) was added, and the mixture was stirred at room temperature overnight. To the reaction mixture was added 1N aqueous sodium hydroxide solution, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (hexane:ethyl acetate). The obtained compound was dissolved in ethyl acetate (20 mL), 4N hydrogen chloride/ethyl acetate (0.5 mL) was added, and the mixture was filtered to give the title compound (652 mg).

Provenance & Evidence