Hydrochloric Acid → HCID 89813901, compound

Participants

Reaction Conditions

Reaction Steps

A resealable tube was charged with (4S)-3-(4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one (See Step 1 in the synthesis of Examples 72 and 73)(50 mg, 0.112 mmol, 50% ee), dioxane (2.647 mL), and water (882 μL). Concentrated HCl (37%) (221 μL) was added, the system was flushed with argon, and the tube was sealed. The reaction mixture was then stirred at 100° C. for 2 hours. LC-MS indicated a clean and complete reaction. After cooling to room temperature, the reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3 solution. The aqueous phase was extracted with EtOAc. The organic phase was concentrated under reduced pressure. The material thus obtained was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 100% MeOH in DCM. The resulting product was then washed with 10% ammonium hydroxide in MeOH. The solution was concentrated under reduced pressure providing (4S)-5,5-dimethyl-3-(4-(6-oxo-5-(pyrimidin-2-yl)-1,6-dihydropyridin-3-yl)cyclohex-3-en-1-yl)-4-phenyloxazolidin-2-one (44 mg, 0.099 mmol, 88% yield, 50% ee) as yellow solid. m/z (ESI) 443.1 (M+H)+.

Provenance & Evidence