Triethylamine → 6-Cyclopentyl-4-hydroxy-6-[4-(3-hydroxy-phenyl)-but-3-ynyl]-3-(thiazol-2-ylsulfanyl)-5,6-dihydro-pyran-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-chloro-6-cyclopentyl-6-[4-(3-hydroxy-phenyl)-but-3-ynyl]-dihydro-pyran-2,4-dione (216 mg, 0.6 mmol) from Step 5 below and 2-mercaptothiazole (141 mg, 1.2 mmol) in DMF (6 mL) was added triethylamine (0.15 mL, 1.2 mmol). The reaction was stirred at 50° C. for 2.5 hours and then quenched with 10 mL of saturated ammonium chloride. The mixture was further acidified to a pH of 1-2 with 1 N HCl. To this mixture was added 10 mL CH2Cl2 and the layers were separated. The aqueous was extracted with 2×10 mL CH2Cl2, and the organic layers were combined. After drying the organic layer over MgSO4, the solids were filtered away and the liquid was concentrated to an oil. The oil was chromatographed on silica to yield the desired product (28 mg, 11% yield). 1H NMR (CDCl3) δ: 1.09-1.58 (m, 8H), 1.93-2.05 (m, 3H), 2.58-2.82 (m, 4H), 6.59 (d, J=6.82 Hz, 2H), 6.65 (d, J=7.58 Hz, 1H), 6.96-7.00 (m, 1H), 7.32 (d, J=3.28 Hz, 1H), 7.46 (d, J=3.28 Hz, 1H). MS (ESI): 440 (M−H).

Provenance & Evidence