Triethylamine → HCID 23614975, compound

Participants

Reaction Steps

To Intermediate 2 (14.8 g, 40 mmol) in THF (200 ml) and triethylamine (44 mmol, 4.45) at 0° C., is added t-butyldimethylsilylchloride (TBDMS-Cl) (44 mmol, 6.63 g). The reaction is allowed to warm to room temperature and stirred overnight. 1 N NaOH solution (100 ml) is added, and the reaction is stirred at 40° C. for 4 h. THF is evaporated under reduced pressure, and the resulting mixture is acidified with 1 N HCl to pH<2. The mixture is extracted with ethyl acetate (2×100 ml). The organic phase is washed with brine solution, dried over MgSO4, and concentrated in vacuo to give 5-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl}-2-chloro-benzoic acid.

Provenance & Evidence