HCID 57857023, compound → HCID 44206775, compound

Participants

Reaction Steps

(Z)-7-((1R,2R,3R)-2-((3R,E)-3-(Benzo[b]thiophen-2-yl)-3-(tetrahydro-2H-pyran-2-yloxy)prop-1-enyl)-5-oxo-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid (33) was dissolved in a 4:2:1 solution of acetic acid-water-THF (0.5 M). The solution was stirred for several days at room temperature until the reaction was complete, as judged by TLC. The crude product was purified by flash chromatography on regular silica gel using ethyl acetate-hexane-0.5% acetic acid as eluent to afford the title compound 14a; TLC: Rf=0.20 (silica on 10 mm aluminum plates, eluent: 40:60:1 hexanes-ethyl acetate-acetic acid); MS (−cESI) m/z 413 (M−1); LC/MS: Sample prep-diluent, methanol. Sample prepared in 100 μL, unknown final concentration, analytical method: column: Phenomenex Synergi Hydro-RP 4p 250×2.00 mm, flow rate 0.2 mL/min, detection UV (210 nm), column temperature 25° C., HPLC mobile phase: isocratic mobile phase consisting of 31.3% solvent A, 68.7% solvent B, Solvent A=10:90:0.1 methanol-water-acetic acid, Solvent B=90:10:0.1 methanol-water-acetic acid.

Provenance & Evidence