Dimethylformamide → HCID 178502407, compound

Participants

Reaction Conditions

Reaction Steps

In an oven-dried 5-mL round bottom flask purged with nitrogen, dissolved the product of Example 218E (50 mg, 0.080 mmol) in anhydrous DMF (1 mL), and cooled to 0° C. Added sequentially (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (29.5 mg, 0.168 mmol), HOBt hydrate (27.6 mg, 0.180 mmol), EDAC (35.3 mg, 0.180 mmol), and N-methylmorpholine (0.035 mL, 0.321 mmol). Stirred the solution at 25° C. for 15 hr. Diluted the reaction in EtOAc (50 mL), washed with sat'd aq NaHCO3 (25 mL), H2O (3×25 mL), and brine (25 mL), dried the organic phase over anhydrous MgSO4, filtered, and concentrated by rotary evaporation to an off-white solid (72 mg). Purified by flash chromatography (silica gel, Alltech Extract-Clean 10 g column, gradient of 6% to 8% MeOH/CH2Cl2) to afford the title compound as an off-white solid (49 mg, 65%). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.82 (d, J=6.72 Hz, 6H), 0.86 (d, J=6.72 Hz, 6H), 1.29 (s, 9H), 1.79-2.01 (m, 5H), 2.03-2.22 (m, 4H), 3.53 (s, 6H), 3.70-3.86 (m, 4H), 4.04 (t, J=8.35 Hz, 2H), 5.04 (dd, J=6.67, 3.20 Hz, 2H), 7.23-7.43 (m, 8H), 7.48-7.60 (m, 4H), 7.61-7.73 (m, 4H), 11.77-12.21 (m, 2H); MS (ESI+) m/z 939 (M+H)+.

Provenance & Evidence