1,2-Dichloroethane → HCID 22977492, 화합물

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A solution of 456 mg (0.088 mmol) of 71 in CH2Cl2 (20 ml) was treated with anhydrous TFA (5 mL) then stirred at room temperature under N2 for 1 hour and evaporated to dryness. The residue was repeatedly concentrated from CH2Cl2 (3×) then dried under vacuum. The resulting residue was dissolved in CH2Cl2 (20 ml), cooled to 0° C., then treated with DIEA (1.3 ml, 8 eq, 2.46 mmol) followed by.4-amino-3-chloro-benzoic acid (202 mg, 1.17 mmol), HOBT (183 mg, 1.35 mmol), and EDC (279 mg, 1.45 mmol). The resulting mixture was allowed to warm to room temperature and stir for 18 hours. The solvent was removed in vacuo and the residue dissolved in EtOAc then washed with distilled water (3×), 0.5N NaHSO4 (2×), saturated NaHCO3 (2×) and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give a residue that was purified by flash chromatography, eluting with CH2Cl2/MeOH (99/1 to 97/3%), affording 285 mg (57% yield) of the title compound (72) as a yellow solid. 1H-NMR (500 MHz, CD3OD) δ 0.91-1.24 (m, 9H), 1.70-2.27 (m, 4H), 2.47-2.85 (m, 1.5H), 2.99-3.13 (m, 0.5H), 3.39-3.53 (m, 0.5H), 3.60-3.78 (m, 1.5H), 3.85-4.04 (m, 1H), 4.24-4.47 (m, 2H), 4.53-4.97 (m, 4H), 5.46 (s, 0.3H), 3.88-4.02 (m, 0.1H), 5.60-5.69 (m, 0.6H), 6.80 (d, 1H), 7.22-7.77 (m, 7H). Analytical HPLC (cyano column) (mixture of 2 diastereomers) 15.90, 16.23 min. LC-MS (ES+) m/e=571.2 (M+H).

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