Tetrahydrofuran → HCID 118062838, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 326B (90 mg, 0.509 mmol), TEA (0.142 mL, 1.018 mmol) in toluene (10 mL) was added DPPA (0.110 mL, 0.509 mmol) and the reaction mixture was stirred at 90° C. for 2 h. The reaction mixture was cooled to RT and to it was added a solution of Intermediate 185B (100 mg, 0.339 mmol) in THF (3 mL) and stirred at RT for 4 h. The reaction mixture was quenched with water and the aq. layer was extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with a 10% aq. solution of NaHCO3 and water, then dried over Na2SO4, filtered and concentrated. The crude reaction material was purified by preparative TLC and was loaded on a 0.5 mm silica gel plate. The plate was developed using 6% MeOH in CHCl3. The band containing the desired product was separated and extracted into 10% MeOH in DCM, and was then filtered and concentrated to afford cis and trans mixture of Compounds 326 and 327 as an off-white solid. The individual isomers were separated by preparative chiral SFC.

Provenance & Evidence