Triethylamine → HCID 59369836, compound

Participants

Reaction Steps

To a solution of racemic 7-3 (6.3 g, 25.6 mmol) in dimethylformamide (100 mL) at 25° C. was added triethylamine (3.88 g, 38.4 mmol) followed by 2-chlorobenzoxazole (5.11 g, 33.3 mmol) and the reaction mixture was stirred at ambient temperature for 24 h. The mixture was diluted with EtOAc (400 mL) and washed with water (4×100 mL). The combined organic layers were dried over MgSO4 and concentrated to an oil. The oil was purified by normal phase silica gel chromatography (0 to 100% EtOAc in hexanes) to afford the racemic product as an oil. ESI+ MS: [M+H]+ 364.3. This material was then separated into its respective enantiomers by the following method: ChiralPak AD 2×25 cm, 10 uM (40:60 hexane:EtOH, 0.1% diethylamine; flow rate=8 mL/min). Enantiomer A Rt=7.3 min; Enantiomer B Rt=8.7 min. 1H NMR (500 MHz, CDCl3) δ 7.43-7.42 (m, 2H), 7.36-7.33 (m, 4H), 7.08-7.02 (m, 3H), 4.64 (m, 1H), 4.52 (m, 1H), 4.43 (m, 2H), 3.42 (m, 1H), 3.29 (m, 1H), 3.14 (m, 1H), 2.71 (s, 3H), 1.84 (m, 1H), 1.60 (m, 1H), 1.43 (m, 1H), 0.560 (m, 1H). HRMS [M+H] C24H23F1N2O2S1 calc'd 423.1537, found 423.1542.

Provenance & Evidence