[O:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.N1CCCC1.O.C1(C)C=CC([S:20](O)(=O)=O)=CC=1.[S].[N:26]#[C:27][NH2:28]>C1CCCCC1.CO>[N:26]1[C:4]2[CH2:3][CH2:2][O:1][CH2:6][C:5]=2[S:20][C:27]=1[NH2:28]To a solution of tetrahydro-4H-pyran-4-one (Aldrich) (7.22 g, 72.11 mmol) in cyclohexane (70 mL) were added pyrrolidine (6.26 mL, 7.57 mmol) and p-toluenesulfonic acid monohydrate (13.72 mg, 0.07 mmol). The reaction mixture was refluxed for 3 hours with a Dean-Stark trap, cooled and concentrated. The residue was dissolved in methanol (20 mL) and then sulfur (2.31 g, 72.11 mmol) was added followed by a solution of cyanamide (3.03 g, 72.11 mmol) in methanol (5 mL) at 0° C. The reaction mixture was stirred at room temperature overnight, filtered, concentrated and purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-5% methanol in dichloromethane) to afford the title compound. MS (ESI+) m/z 157 (M+H)+.
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