p-Toluenesulfonic acid monohydrate → Adamantane-1-carboxylic acid [3-(2-methoxyethyl)-4,6-dihydro-3H-furo[3,4-d]thiazol-2-ylidene]-amide

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Reaction Steps

To a solution the product of Example 72D (15 mg, 0.04 mmol) in toluene (10 mL) was added p-toluenesulfonic acid monohydrate (2 mg). The solution was heated at reflux for 3 hours and then cooled to room temperature, diluted with ethyl acetate, washed with 1M aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. Purification by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes afforded 4 mg (30%) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.61-1.76 (m, 6 H), 1.82-1.88 (m, 6 H), 1.93-2.02 (m, 3 H), 3.24 (s, 3 H), 3.63 (t, J=5.0 Hz, 2 H), 4.18 (t, J=5.0 Hz, 2 H), 4.91 (s, 4 H); MS (ESI+) m/z 363 (M+H)+;

Provenance & Evidence