Methanol → tert-Butyl (3-{cyclopropyl {3-(3-methoxypropyl)-5-[3-(methylsulfonyl)propoxy]benzyl}amino)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

Participants

Reaction Steps

To tert-butyl (3-{cyclopropyl{3-(3-methoxypropyl)-5-[3-(methylthio)propoxy]benzyl}amino)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate from Example 75, Step 2 (1 eq.) in a 1:1 (v/v) methanol:water solution (0.05 M) was added Oxone™ (2.5 eq.) and sodium bicarbonate (10 eq.). The reaction mixture was stirred at RT for 1 h. The volatiles were then removed in vacuo and the result residue was extracted with ether. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 3:2 (v/v) Hex:EtOAc→1:3 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Provenance & Evidence