Hydrochloric Acid → HCID 59551959, compound

Participants

Reaction Steps

To a stirred solution of XII (3.12 Kg) in ethanol (36 L), a glucose solution (2.496 Kg in 15.6 L 2N NaOH) was added dropwise under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 24 hr. Zinc powder (5.46 Kg) previously activated with HCl solution was charged portionwise to the reaction mixture. The reaction mixture was heated at 60° C. for 4 hr to 6 hr until N-Oxide completely consumed. The reaction mixture was cooled and extracted with 15 liters of a 2:1 hexane:toluene mixture. The organic layer was separated and the aq. layer was re-extracted with a 2:1 hexane:toluene mixture (15 L×3). The organic layer was combined and evaporated up to 90% volume. Upon standing at room temperature the organic layer was solidified. The solid was purified by the slurry wash with 5 L of a 95:5 hexane:toluene mixture followed by a methanol slurry wash (3 L) to give title compound (XIII) (1.34 Kg).

Provenance & Evidence