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ChemicalBook CAS DataBase List Benzoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-5-methoxy- (9CI)
262614-64-2

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

1synthesis methods
24424-99-5 Synthesis
Di-tert-butyl dicarbonate

24424-99-5
858 suppliers
$13.50/25G

6705-03-9 Synthesis
2-Amino-5-methoxybenzoic acid

6705-03-9
276 suppliers
$9.00/1g

-

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]

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