Hydrochloric Acid → 2-Cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethanesulfonic acid thiazol-2-ylamide

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (1.0 mmol, 0.10 g) in 7 mL of THF and 3 mL of DMPU at 0° C. is added n-BuLi (0.61 mL, 2.5 M in hexane) and the reaction mixture is stirred for 15 min, then cooled to −78° C. The title C compound, C-(4-methane-sulfonyl-phenyl)-N-thiazol-2-yl-methanesulfonamide (0.693 mmol, 0.23 g) is added and the reaction mixture is allowed to warm to 0° C. After 1 h, the reaction is recooled to −78° C., cyclopentylmethyliodide (0.72 mmol, 0.15 g) is added and the reaction is allowed to warm to RT over 3 h. The reaction mixture is poured into aqueous 1 N HCl, and the product is taken up in EtOAc, dried and evaporated to afford an orange oil. Chromatography on silica affords 2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethanesulfonic acid thiazol-2-ylamide: 1H NMR δ 11.6 (br s, 1H), 7.84 (d, J=8, 2H), 7.58 (d, J=8, 2H), 6.67 (d, J=4.5, 1H), 6.39 (d, J=4.5, 1H); 4.27 (m, 1H), 3.03 (s, 3H), 2.04-2.2 (m, 1H), 1.12-1.61 (m, 10H); e/z (ES) 415 (M+1, 100%).

Provenance & Evidence