Methanol → HCID 72758525, compound

Participants

Reaction Conditions

Reaction Steps

DIEA (0.1 mL, 0.58 mmol, 1 equiv) and R(+)-propylene oxide (3 mL) were added to a stirred cool solution of crude 4-pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide (307.6 mg, 0.58 mmol, 1 equiv), prepared as in Example 10, in anhydrous methanol (10 mL), at 0° C. and under nitrogen. The resulting solution was stirred at −4° C. for 18 h and evaporated to dryness. The residue obtained was purified by chromatography over silica gel, with an eluent of 6% methanolic ammonia in dichloromethane. The desired fractions were evaporated, and lyophilized (deuterium oxide/anhydrous acetonitrile, 1:1, v/v, 20 mL) to furnish the title compound as a fluffy white powder (91 mg, 48%).

Provenance & Evidence