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A solution of DPPA (4.812 g, 17.494 mmol) in toluene (24 mL) was added dropwise at room temperature to a solution of compound SP-0010418-145-3 (2.8 g, 15.9 mmol) in DCM (80 mL) and triethylamine (4.0 mL). The mixture was stirred at 50 °C for 1 h, and more toluene (50 mL) was added. The resulting reaction mixture was heated at 85 °C for 3 h. The reaction mixture was cooled down to room temperature, aqueous HC1 (6.0 N, 28 mL) was added and the resulting reaction mixture was heated at reflux for an additional3 h. The organic layer was separated, washed with saturated NaHCO3, dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (using petroleum ether/EtOAc = 10:0 ? 7:3) to give compound SP-0010418-145-4 (2.0 g, yield: 85percent). ?H NMR (400 MHz, CDC13): oe 7.55- 7.51 (m, 1 H), 7.24-7.22 (m, 1 H), 87.06-7.03 (m, 1 H), 7.4.42 (s, 2 H), 3.61 (s, 2 H).
Example 1B (3.472 g, 19.7 mmol) was dissolved in dichloromethane (45 mL) to which was added triethylamine (3.5 mL) and diphenylphosphoryl azide (5.97 g, 21.7 mmol) in toluene (20 mL). The flask was equipped with a Dean-Stark trap and the mixture was heated to reflux. Toluene (45 mL) was added after one hour and the mixture was reflux for an 2 additional hours after which it was cooled to ambient temperature. 6N hydrochloric acid (50 mL) and toluene (20 mL) were added and the biphasic mixture refluxed for 3.5 hours followed by cooling to ambient temperature. Ethyl acetate (100 mL) and water (100 mL) were added, and the separated organic layer was washed sequentially with saturated sodium bicarbonate (2*100 mL), brine, dried over anhydrous sodium sulfate and filtered. The solution was concentrated under reduced pressure and chromatographed on silica gel eluding with 0-to-40percent ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) delta ppm 3.68 (s, 2H), 4.46 (s, 2H), 7.04 (m, 2H), 7.23 (m, 2H). MS (DCI) m/z 148.04 (M+NH4-H2O)+.
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