Hydrochloric Acid → HCID 23394561, compound

Participants

Reaction Steps

Intermediate 2 (31.0 g) was introduced dropwise to a well-stirred solution of Intermediate 16 (50.0 g) in ethyl acetate (500 mL) and triethylamine (25 mL). The reaction temperature was kept below 25° C. throughout by external cooling. Acylation of the starting material was complete after a 1.5 hour stir-out. Water (150 mL) was charged at the end of this period, followed by sufficient 2M hydrochloric acid to lower the pH to 1-1.5. Following separation, the organic phase was washed with water (2×150 mL), 5% sodium carbonate solution (150 mL) and 10% brine (2×150 mL) then dried (MgSO4), filtered and evaporated in vacuo to afford the title compound as a yellow-brown foam (71.1 g, 95.6% yield). 1H NMR D6-DMSO: δ1.1-1.73 (10H, b,m); 2.98 (1H, dd); 3.20 (1H, dd); 3.64 (2H, m); 4.13 (2H, t); 4.24 (1H, m); 4.39 (1H, s); 4.87 (1H, t); 7.28 (2H, d); 7.59 (2H, d); 8.37 (1H, d); 8.81 (2H, s); 10.88 (1H, s) ppm. Mass Spectrum: ESI+ m/z 532/534

Provenance & Evidence