Synthetic Route of 681465-85-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 681465-85-0 name is Methyl 4-amino-3-isopropoxybenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
4-(2-(Benzyloxy)-3-isopropoxy-4-nitrobenzamido)-3-isopropoxybenzoate 2-Benzyloxy-3-isopropoxy-4-nitrobenzoic acid (51.5 mg, 0.16 mmol) was dissolved in CH2Cl2 (8 mL) and preactivated with Ghosez’s reagent (66.0 muL, 0.50 mmol) for 3 hours at 40 C. 3-Isopropoxy-4-aminomethylbenzoate (0.12 g, 0.55 mmol) was dissolved in CH2Cl2 (8 mL) and N,N-diisopropylethylamine (DIPEA) was added (0.20 mL, 1.12 mmol). The solution containing the acid chloride was then added and the reaction mixture stirred for 2 days at 40 C. The solvent was then removed and the crude product was purified by preparative HPLC (RP-18; run time 100 min; H2O/MeCN=100:0?0:100; tr=80 min) providing the title compound (56.9 mg, 0.11 mmol, 68%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) delta 10.33 (s, 1H-NH), 8.55 (d, J=8.5 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.70 (dd, J=8.5, 1.7 Hz, 1H), 7.59 (d, J=8.7 Hz, 1H), 7.57 (d, J=1.7 Hz, 1H), 7.25-7.12 (m, 5H), 5.25 (s, 2H), 4.75-4.67 (m, 1H), 4.67-4.59 (m, 1H), 3.93 (s, 3H), 1.40 (d, J=6.2 Hz, 6H), 1.28 (d, J=6.0 Hz, 6H) ppm. 13C NMR (100 MHz, CDCl3) delta 167.0, 161.4, 151.1, 147.9, 146.1, 145.2, 134.1, 132.9, 132.9, 130.0, 129.4, 128.7, 125.79, 125.6, 123.3,120.1, 119.5, 113.3, 78.9, 77.4, 71.7, 52.3, 22.6, 22.1 ppm. HRMS (ESI): Calculated for C28H31N2O8 (M+H+: 523.2080. found: 523.2075.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-3-isopropoxybenzoate, and friends who are interested can also refer to it.
Reference:
Patent; HELMHOLTZ-ZENTRUM FUeR INFEKTIONSFORSCHUNG GMBH; GOTTFRIED WILHELM LEIBNIZ UNIVERSITAeT HANNOVER; Baumann, Sascha; Herrmann, Jennifer; Mohr, Kathrin; Steinmetz, Heinrich; Gerth, Klaus; Raju, Ritesh; Mueller, Rolf; Hartmann, Rolf; Hamed, Mostafa; Elgaher, Walid A.M.; Moreno, Maria; Gille, Franziska; Wang, Liang Liang; Kirschning, Andreas; (196 pag.)US2016/145304; (2016); A1;,
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