Thionyl Chloride → HCID 11322807, compound

Participants

Reaction Steps

Charge a 500 mL three neck flask equipped with a condenser, nitrogen inlet and a thermometer with ditert-butyl (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate (15 g, 36.4 mmol) in ethanol (365 mL). Add thionyl chloride (13.3 mL, 182.3 mmol) to a stirring solution at room temperature via syringe (small exotherm) then heat to reflux. After 24 hours cool the reaction to room temperature and concentrate in vacuo. Dissolve the residue in dichloromethane (50 mL) then concentrate on a rotary evaporator (repeat 3 times). Partition the residue between ethyl acetate (200 mL) and saturated sodium hydrogenate carbonate (150 mL). Wash the organic phase with brine (150 mL), dry over sodium sulfate, filter then concentrate to dryness to give the title compound as an oil (8.24 g, 32.3 mmol). MS (m/z): 256 (M+1).

Provenance & Evidence