Tetrahydrofuran → HCID 118061924, compound

Participants

Reaction Steps

A solution of Intermediate 320B (83 mg, 0.509 mmol), TEA (0.142 mL, 1.018 mmol) and DPPA (0.11 mL, 0.509 mmol) in toluene (10 mL) was heated to 90° C. and stirred 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 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 layer was washed with a 10% aq. solution of NaHCO3 and then water, dried over Na2SO4, filtered and concentrated. The crude material was purified by preparative TLC and was loaded on a 0.5 mm silica gel plate and developed using 6% MeOH in CHCl3. The band containing the desired product was separated and extracted into 10% MeOH in DCM, then was filtered and concentrated to afford mixture of 320 and 321 as an off-white solid. The individual isomers were separated by preparative chiral SFC.

Provenance & Evidence