Tetrahydrofuran → HCID 118062783, compound

Participants

Reaction Steps

A solution of Intermediate 252B (54.3 mg, 0.361 mmol), TEA (0.076 mL, 0.542 mmol) and DPPA (0.078 mL, 0.361 mmol) in toluene (5 mL) was stirred at 90° C. for 1.5 h. The reaction mixture was cooled to RT and in to it was added a solution of Intermediate 185B (50 mg, 0.181 mmol) in THF and stirred at RT for 4 h. The reaction mixture was quenched with water and extracted with ethyl acetate (3×5 mL). The combined organic layer was washed with a 10% aqueous solution of NaHCO3, water, and then dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified by preparative TLC. The crude material was loaded on a 0.5 mm silica gel plate and developed using 6% MeOH in CHCl3. Band containing desired product was removed and extracted into 10% MeOH in DCM, filtered and concentrated to offered Compounds 252 and 253 as off-white solid (mixture of cis and trans isomers). Both isomers were separated by chiral SFC.

Provenance & Evidence