Hydrochloric Acid → HCID 54018908, compound

Participants

Reaction Steps

A solution of (+/-)-2-[2-(3-cyclopentyloxy-4-methoxyphenyl)-4-phenylbut-3-ynyl]-4-hydroxy-5-methyl-4,5-dihydrothiazole (70 mg, 0.2 mmol) in CDCl3 (4 ml) was treated with HCl (0.2 ml of a 1N solution in Et2O) and heated to 50° for 3 hr. The solvent was evaporated, the residue taken up in Et2O, washed with aqueous NaHCO3, H2O, dried and the solvent evaporated. Purification by flash chromatography (silica gel, 2% Et2O in CH2Cl2) gave the titled compound (19 mg, 28%). 1H NMR (400 MHz, CDCl3) δ 7.42 (m, 2 H), 7.36 (s, 1 H), 7.30 (m, 3 H), 7.00 (m, 1 H), 6.92 (d, 1 H), 6.84 (d, 1 H), 4.74 (m, 1 H), 4.28 (t, 1 H), 3.82 (s, 3 H), 3.40 (d, 2 H), 2.42 (s, 3 H), 1.78-1.98 (m, 6 H), 1.60 (m, 2 H).

Provenance & Evidence