These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-aminobenzoate, its application will become more common.
4518-10-9,Some common heterocyclic compound, 4518-10-9, name is Methyl 3-aminobenzoate, molecular formula is C8H9NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
EXAMPLE 13-[2-(2,4,6-Trihydroxy-phenyl)-acetylamino]-benzoic acid (18)SCLiOH H2O/TIH F EPO Step 1: (The following reaction is done in an anhydrous N2 atmosphere.) Dissolve EDC hydrochloride (122mg, 0.64mmol) and triethylamine (89muL, 0.64mmol) in anhydrous dichloromethane (3.2mL) and stir for 5min at rt. Add 2-(2,4,6-Trimethoxyphenyl)- acetic acid (14) (lOlmg, 0.45mmol) and DMAP (8mg, O.Ommol) and stir for lOmin. Add ethyl ester (15) (70mg, 0.42mmol) and stir the reaction solution overnight at rt. Hydrolize the reaction solution with saturated aqu. NH4Cl followed by water, separate layers, extract aqu. layer with dichloromethane (3 times) and wash the combined organic layers with water and brine and dry with Na2SO4. Remove solvent under reduced pressure. Purify crude product by preparative radial chromatography (silica gel 60PF, EtOAc/CyH 1+1) to obtain 3-[2- (2,4,6-Trimethoxy-phenyl)-acetylamino]-benzoic acid methyl ester (16) as a white solid (145mg, 95%). [K. C. Nicolaou; P. S. Baran; Y.-L. Zhong; K. Sugita; J Am. Chem. Soc; 2002; 124; 10; 2212-2220]. 1H NMR (400MHz, CDCl3): 3.68 (s, 2 H); 3.83 (s, 3 H); 3.84 (s, 6 H); 3.87 (s, 3 H); 6.18 (s, 2 H); 7.33 (t, 1 H, J= 8.0Hz); 7.56 (br.s, 1 H); 7.69 (br.dd, 1 H, J= 7.8Hz); 7.78 (t, 1 H, J= 1.8Hz); 7.90 (dd, I H1 J/ = 8.1Hz, J2 = 1.3Hz).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-aminobenzoate, its application will become more common.
Reference:
Patent; REVOTAR BIOPHARMACEUTICALS AG; WO2007/39112; (2007); A1;,
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