Propionic Acid → HCID 78028916, compound

Participants

Reaction Conditions

Reaction Steps

To an orange solution containing 3-(((7-methyl-3-neopentyl-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)amino)-4-nitrobenzonitrile (0.100 g, 0.241 mmol) in 1-propanol (2.41 mL) was added iron (325 mesh) (0.135 g, 2.41 mmol), trimethyl orthopropionate (0.324 g, 2.41 mmol), and propionic acid (0.179 g, 2.41 mmol). The reaction mixture was stirred at 65° C. for 2 h and then cooled to rt. The reaction was diluted with MeCN (2 mL) and filtered through an Acrodisc CR 25 mm syringe filter with a 0.2 μm PTFE membrane. The filtered solution was purified by reverse-phase HPLC (Sunfire Prep C18 (30×150 mm); Solvent A: MeCN/0.1% TFA, Solvent B: water/0.1% TFA; gradient: 25-55% solvent A over 15 min; 25 mL/min elution; 220 nm detection) to afford the title compound (0.092 g, 69% yield) as the TFA salt. 1H NMR (400 MHz, CDCl3) δ 8.07 (br. s., 1H), 7.83 (s, 1H), 7.69-7.79 (m, 1H), 4.08 (s, 2H), 3.32 (dd, J=8.78, 35.39 Hz, 2H), 3.01 (dd, J=14.05, 43.42 Hz, 2H), 2.05 (d, J=13.55 Hz, 1H), 1.85-1.99 (m, J=12.55 Hz, 2H), 1.48-1.77 (m, 5H), 1.20-1.44 (m, 8H), 0.96 (s, 9H). MS (m/z) 423.3 (M+H+).

Provenance & Evidence