Diisopropyl azodicarboxylate → (5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-[(5-Ethyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-one

Participants

Reaction Steps

5-Ethyl-1H-tetrazole (0.164 g, 1.67 mmol), (5R)-3-[4-(1,1-dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-(hydroxymethyl)oxazolidin-2-one (WO 01/81350 A1) (0.30 g, 0.84 mmol), and polystyrene-triphenylphosphine (1.73 mmol/g loading: Argonaut Technologies, Inc. Foster City, Calif. USA, 1.46 g, 2.53 mmol) were dissolved in dry dichloromethane (30 ml). Diisopropylazodicarboxylate (0.33 ml, 1.68 mmol) was added and the mixture was stirred at room temperature for 16 hours. The resin was filtered off and rinsed with dichloromethane. The filtrate was evaporated to dryness and purified by chromatography on silica gel with 10% acetonitrile in dichloromethane. The material obtained after chromatography was precipitated from dichloromethane with diethyl ether to yield the title compound as a white powder (0.26 g, 71%).

Provenance & Evidence