Triethylamine → HCID 11561276, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of benzoic acid from Example 92A (255 mg, 0.56 mmol) in 5 mL of anhydrous THF at 0° C. was added in turn Et3N (102 mL, 0.73 mmol) and ethyl chloroformate (70 mL, 0.73 mmol). After 60 minutes, the reaction mixture was filtered through celite plug into a stirred solution of NaBH4 in water at 0° C. The resulting reaction mixture stirred at 0° C. for 2 hours before it was extracted with EtOAc (2×20 mL). The combined organic layers were washed with 3N HCl, brine, dried over Na2SO4, filtered, concentrated under reduced pressure. The crude product was purified using Gilson Preparative HPLC as described in Example 38B to give the title compound (80 mg, 32% yield) as a light-yellow solid. 1H NMR (d6-DMSO, 300 MHz) δ 2.04 (s, 3H), 3.40-3.79 (m, 8H), 4.56 (s, 2H), 5.38 (br s, 1H), 6.85 (d, J=8.7 Hz, 1H), 7.42 (d, J=15.6 Hz, 1H), 7.52 (br s, 3H), 7.57 (br s, 2H), 7.91 (dd, J=2.1, 8.7 Hz, 1H), 8.66 (d, J=2.1 Hz, 1H). MS (APCI+) (M+NH4)+ at m/z 459.

Provenance & Evidence