4-Methylmorpholine → HCID 21092742, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[2-(5-phenyl-1,3,4-thiadiazole-2-sulfonylamino)-ethyl]-N-[(thymin-1-yl)-acetyl]-glycine (1.02 g, 2 mmol) in tetrahydrofuran (50 mL) was added N-methylmorpholine (3.3 mL, 3 mmol) and then the mixture was cooled to −20° C. After stirring for 5 min at the same temperature, isobutyl chloroformate (3.4 mL, 26 mmol) was added to the reaction mixture. The resulting mixture was slowly warmed to 0° C. for 1 hour. Then the reaction mixture was evaporated in vacuo and dissolved in a mixture of ethyl acetate and acetonitrile. The solution was washed with brine and dried over sodium sulfate and filtered. The filtrate was evaporated in vacuo and triturated with tetrahydrofuran-ethyl ether (1/1, v/v) to precipitate solid. The solid was filtered off, washed with ethyl ether, and dried in vacuo to give the titled compound (883 mg, 90%). 1H NMR (500 MHz; DMSO-d6) δ 11.30 (s, 0.6H), 11.29 (s, 0.4H), 8.10 (d, 2H), 7.68–7.57 (m, 3H), 7.33 (s, 0.6H), 7.27 (s, 0.4H), 4.66 (s, 1.2H), 4.58 (s, 0.8H), 4.43 (s, 0.8H), 4.30 (s, 1.2H), 4.17 (t, 1.2H), 4.02 (t, 0.8H), 3.95 (t, 1.2H), 3.85 (t, 0.8H), 1.73(s, 3H).

Provenance & Evidence