With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1229006-21-6, name is Methyl 3-(benzyloxy)-5-((2,4-difluorobenzyl)carbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate, molecular formula is C26H26F2N2O7, molecular weight is 516.4907, as common compound, the synthetic route is as follows.Application In Synthesis of Methyl 3-(benzyloxy)-5-((2,4-difluorobenzyl)carbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate
Example 2e Methyl 5-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-1-[2-hydroxy-2-(methyloxy)ethyl]-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate (in equilibrium with the corresponding aldehyde) Methyl 1-[2,2-bis(methyloxy)ethyl]-5-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate 25 (11.6 g) was treated with 90% formic acid (250 mL) at 40 C. for ?12 hours (monitored by LC-MS). After the solvents were evaporated at <40 C., the residue was re-dissolved in EtOAc (?1 L) and the resulting solution was washed with NaHCO3 and brine. The organic phase was then dried over Na2SO4. After evaporation of solvents, the titled compounds 26 and 27 were obtained as an approximate 80/20 equillibrium mixture (10.57 g). 1H NMR (400 MHz, DMSO-d6) 5 ppm 10.3 (m, 1H), 9.47 (s, aldehyde-H. ?0.2H)), 8.4 (m, 1H), 7.3 (s, 6H), 7.2 (m, 1H), 7.0 (m, 1H), 6.3 (m, 2H), 5.1 (s, 3H), 4.9 (m, 1H), 4.5 (m, 3H), 3.9 (m, 2H), 3.8 (s, 3H). LC-MS, for 26 (M+H+), calcd 503, obsd 503; for 27 (M+H2O+H+), cald 489, obsd 489.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,1229006-21-6, Methyl 3-(benzyloxy)-5-((2,4-difluorobenzyl)carbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate, and friends who are interested can also refer to it.
Reference:
Patent; SHIONOGI & CO., LTD.; ViiV Healthcare Company; Kawasuji, Takashi; Nagamatsu, Daiki; (30 pag.)US9242986; (2016); B2;,
Pyridine – Wikipedia,
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