Benzoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-5-methoxy- (9CI) synthesis

Yield:262614-64-2 78%

Reaction Conditions:

with pyridine at 90; for 2.5 h;

Steps:

4.1.2. General method for the synthesis of compounds 11, 12 and 14

General procedure: Di-tert-butyl dicarbonate (Boc2O) (1.1 eq) was added to a solutionof the appropriate amine (1 eq) dissolved in anhydrous pyridine(C 1 M). The mixture was stirred at 90 °C for 1h30, then Boc2O (0.5 eq) was added and the mixture was stirred at 90 °C for1 h. The reaction mixture was quenched with aqueous saturatedNH4Cl, the product was then extracted with EtOAc (3 times) andwashed twice with aqueous saturated NH4Cl, and then once withbrine. The organic layer was dried over MgSO4 and concentrated invacuo. The residue was purified by preparative HPLC to give thedesired product.

References:

Baulard, Alain R.;Biela, Alexandre;Blaise, Mickael;Bourbiaux, Kevin;Cantrelle, Francois-Xavier;Djaout, Kamel;Flipo, Marion;Frita, Rosangela;Hanoulle, Xavier;Herledan, Adrien;Kremer, Laurent;Leroux, Florence;Moune, Martin;Pintiala, Catalin;Piveteau, Catherine;Tanina, Abdalkarim;Vandeputte, Alexandre;Willand, Nicolas;Déprez, Benoit;Fa?on, Léo;Wintjens, René [European Journal of Medicinal Chemistry,2020,vol. 200]