Hydrochloric Acid → HCID 90162827, compound

Participants

Reaction Steps

To a stirred solution of carboxylic acid 9 (50 mg, 100.9 μmol) in 5 ml dry THF under argon atmosphere at −60° C. was added N-methylmorpholine (14 μl, 126.3 μmol, 1.25 equiv.) and isobutyl chloroformate (14.9 μl, 116.7 μmol, 1.15 equiv.). After 30 min an etheral solution of diazomethane (0.95 ml 0.6 M, 0.57 mmol, 5.6 equiv.) was added to above solution at −60° C. and the reaction mixture was stirred for 1 hr. A 1:1 solution of conc. HCl and glacial acetic acid was added dropwise to the reaction mixture, before ethyl acetate and water were added. The organic layer was washed with brine, sat. aq. NaHCO3 and dried over MgSO4. Concentration in vacuo afforded the crude title compound, which was used without purification. 1H NMR (400 MHz, CDCl3+MeOD) δ ppm 7.89 (dd, J=1.5 Hz, J=3.0 Hz, 1H), 7.71 (s, 1H), 7.39 (dd, J=1.2 Hz, J=5.2 Hz, 1H), 7.36 (dd, J=2.9 Hz, J=5.2 Hz, 1H), 7.06 (s, 1H), 5.59 (dd, J=4.6 Hz, J=10.0 Hz, 1H), 4.80 (s, 1H), 4.17 (s, 2H), 3.06 (m, 2H), 2.83 (m, 2H), 2.30 (m, 1H), 2.11 (m, 1H), 1.88 (s, 3H), 1.48 (m, 2H), 1.42 (s, 9H), 1.34 (m, 1H), 1.22 (m, 1H), 0.99 (d, J=6.8 Hz, 3H), 0.80 (d, J=6.8 Hz, 3H). MS (ESI): m/z calcd for C24H36C1N5O4S+H+ 526.2 [M+H]+. found 526.3.

Provenance & Evidence