p-Toluenesulfonic acid monohydrate → 1,3,4-Thiadiazole-2-ethanol, beta-amino-beta-methyl-5-[4-(octyloxy)-3-(trifluoromethyl)phenyl]-, (betaS)-

Participants

Reaction Conditions

Reaction Steps

A 5 L round bottom flask was inerted and charged with p-toluene sulfonic acid monohydrate (208 g, 1.09 mol, 5 equiv) and a solution of (R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)oxazolidine-3-carboxylate (125 g, 0.22 mol) in methanol (2.5 L), and heated to reflux. After 1.5 h HPLC indicated reaction complete. The heat was turned off and the mixture was allowed to cool to room temperature (18 to 23° C.) and stirred for 12 hours. The mixture was concentrated under vacuum to a residue to provide the title product.

Provenance & Evidence