Methanesulfonyl chloride → HCID 86635929, compound

Participants

Reaction Conditions

Reaction Steps

N-Cyclopropyl-N-(2,3-dichlorobenzyl)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-4-hydroxybutanamide from the previous step (1 eq.) and Hunig's base (3.5 eq.) were combined in CH2Cl2 (0.024 M). At −78° C., methanesulfonyl chloride (1.5 eq) was added and the reaction mixture was stirred at −78° C. for 10 min and at 0° C. for 10 min. The resulting mixture was quenched with sat. aq. NaHCO3 and extracted with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered and the filtrate concentrated in vacuo. The resulting residue was taken up in DMF (0.06 M) and added sodium azide (5 eq). This mixture was then allowed to stir at RT for 24 h. The resulting mixture was poured into water and 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 column chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a viscous oil.

Provenance & Evidence