Hydrochloric Acid → 6-[3-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydro-Naphthalen-2-yl)-Ureido]-Nicotinic Acid

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Reaction Steps

A solution of methyl 6-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-nicotinate (55) (37 mg) in 5 mL THF, 2 mL methanol and 2 mL water was treated with lithium hydroxide hydrate (50 mg), stirred at room temperature for two hours. The reaction mixture was diluted with 5 mL water, the pH adjusted to 2 with concentrated HCl and extracted with three 10 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo, to give a pale yellow solid. The product was purified by flash chromatography (SiO2, 10% methanol/dichloromethane) followed by trituration in hexanes, yielding 17 mg 6-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl) -ureido]-nicotinic acid (49) as a white solid. M.P. 175-179.5° C.

Provenance & Evidence