Methanol → (2S,3R,4S,5S,6R)-2-((4-(4-((E)-4-(2,9-Diazaspiro[5.5]undecan-2-yl)but-1-en-1-yl)-2-methylbenzyl)-5-isopropyl-1H-pyrazol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Participants

Reaction Steps

Add methanol (5 mL), triethylamine (3 mL), and water (3 mL) to 4-{4-[(1E)-4-(2,9-diazaspiro[5.5]undec-2-yl)but-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside dihydrochloride (480 mg, 0.24 mmol). After 18 hours (overnight) at room temperature, concentrate to dryness under reduced pressure. Purify the resulting residue by preparative HPLC method: high pH, 25% B for 4 min, 25-40 B % for 4 min @85 mL/min using a 30×75 mm, 5 um C18XBridge ODB column, solvent A—H2O w NH4HCO3@pH 10, solvent B—MeCN to yield the title compound as a solid (50 mg, 0.08 mmol).

Provenance & Evidence