Hydrochloric Acid → N-(3-benzoylphenyl) N-methyl 2-(3-pyridinyl)-4-thiazolidinecarboxamide dihydrochloride

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Reaction Steps

Hydrochloric acid in dioxane (4M, 10 mL) was added to N-(3-benzoylphenyl) N-methyl 2-(3-pyridinyl)-3-tert-butoxycarbonyl-4-thiazolidinecarboxamide (0.64 g) in dioxane (3 mL). The reaction mixture was concentrated and the residue partitioned between ethyl acetate and saturated aqueous sodium carbonate. The organic layer was washed with saturated aqueous sodium carbonate and dried over magnesium sulfate. The solvent was removed in vacuo and the residue chromatographed on silica gel, eluting with ethyl acetate to give the desired compound as a colorless oil (417 mg, 81%). This was converted to the dihydrochloride salt using the method of example 3. NMR (CDCl3, 300 MHz): δ2.72-3.28 (c, 3H), 3.42-3.97 (c, 4H), 5.57 (s, 0.6H), 5.61 (s, 0.4H), 7.21-7.48 (c, 6H), 7.81 (m, 1H), 8.51 (dd, 0.4H, J=1.0, 8.0), 8.56 (dd, 0.6H, J=1.0, 8.0), 8.72 (m, 1H). Mass Spectrum (DCI/NH3): 286 (M+H)+.

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