Ethyl chloroformate → HCID 58968700, compound

Participants

Reaction Steps

To a suspension of N-(2-(4-methoxypiperidin-4-yl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2-methyl-2H-tetrazol-5-amine (31 mg; 0.049 mmol) in methylene chloride (0.5 mL) was added diisopropylethylamine (0.05 mL; 0.287 mmol). Ethyl chloroformate (10uL; 0.104 mmol) was then added. The resulting reaction was stirred at room temperature for 16 hours. The reaction was filtered over a column of silica/sodium sulfate and concentrated under reduced pressure. The residue was purified by 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (30-85% ethyl acetate in heptane) to give 32 mg (98%) of a gum. MS (ES+): Calc: 668.5, Found: 669.6 (M+H), 1H NMR (400 MHz, CDCl3) δ ppm 7.79 (s, 1H), 7.73 (s, 2H), 7.51 (d, J=6.64 Hz, 1H), 7.50 (s, 1H), 7.36 (d, J=8.71 Hz, 1H), 5.10 (s, 2H), 4.82 (s, 2H), 4.2 (s, 3H), 4.14 (q, J=7.05, 2H), 4.02 (bm, 2H), 3.16 (t, J=12.45 Hz, 2H), 2.95 (s, 3H), 2.14 (m, 2H), 1.9-1.63 (m, 2H), 1.27 (t, J=7.05 Hz, 3H).

Provenance & Evidence