1,2-Dichloroethane → HCID 52932105, compound

Participants

Reaction Steps

To a solution of 0.05 g (0.24 mmol) 1,1′-biphenyl-4-ylacetic acid in 0.50 ml DMF was added 0.05 g (0.24 mmol) 2-[(1R)-1-ammonioethyl]-5-methyl-1,3-thiazol-3-ium dichloride, 0.04 g (0.31 mmol) HOAT, 0.60 g (0.31 mmol) EDC, and 0.12 mL (0.71 mmol) DIEA. After 24 h at room temperature, the reaction mixture was purified by preparative HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18) to afford 0.70 g (86%) 2-(biphenyl-4-yl)-N-[(1R)-1-(5-methyl-1,3-thiazol-2-yl)ethyl]acetamide. 1H NMR (CDCl3, 400 MHz) 7.59 (m, 4H), 7.44 (m, 2H), 7.35 (m, 4H), 6.55 (br d, 1H, J=7.32 Hz), 5.43 (m, 1H), 3.65 (s, 2H), 2.43 (s, 3H), 1.55 (d, 3H, J=6.96 Hz). HRMS (ES) [M+1]+ calcd for C20H21N2OS: 337.1375. Found: 337.1368.

Provenance & Evidence