Electric Literature of 764659-72-5, 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.764659-72-5, name is (2R,5S)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate, molecular formula is C18H26FN3O4S, molecular weight is 399.4802, as common compound, the synthetic route is as follows.
EXAMPLE-13: Synthesis of 4-amino-5-fluoro-1-(2 ?-hydroxymethyl-[1,3]-oxothiolane- 5S-yl)1tf-pyrimidin-3-one. 2-fluorobenzoic acid salt (formula-8b1); Dipotassium hydrogen orthophosphate (83.3 g) was dissolved in a mixture of industrially methylated spirit (IMS, 600 mL) & purified water (200 mL) and the obtained solution was cooled to 18C. The compound of formula-7b (100 g, 0.26 mol) was added at 15-22C and the suspension was stirred at 18-22C for 1 h. A solution of sodium borohydride (20. 4 g (0.54 mol) in water (110 mL) containing sodium hydroxide (40 mg)) was added drop wise by keeping temperature at 18-22C and maintained for 4 h. The completion of the reaction was confirmed by TLC. The reaction mass was transferred into a separating funnel and the layers were separated. The organic layer pH was adjusted to 5.9-6.3 with aq. HCI (~25 mL) and readjusted to pH 7.5-7.8 with sodium hydroxide (15 mL, 15% w/w) and filtered. IMS (~790 mL) was distilled out initially atmospherically followed by reduced pressure to reduce the traces of IMS. The resultant residue was diluted with water (200 mL) and then cooled to 22-30C. Toluene (150 mL) was added to the reaction mass under stirring, allowed the layers to settle and separate the layers. Toluene layer was washed with water (100 mL) and combined aqueous layer was charcoalized. The filtrate was warmed to 38-42C, 2- fluorobenzoic acid (37 g, 0.26 mol) was added and stirred for 2h at the same temperature. The reaction mass was cooled to 22-30C and maintained for 3-4h. The separated solid was filtered and washed with pre-cooled water and dried to get compound of formula-8b. in 80 g. 1H NMR (300 MHz, DMSO-d6): delta 13.40 (brs, 1H), 8.20 (d, 1 H, J=7.2 Hz), 7.84-8.00 (m, 2H), 7.58-7.68 (m, 2H), 7.28-7.34 (m, 2H), 6.12-6.16 (m, 1H), 5.41 (t, 1 H, J=5.4 Hz), 5.18-5.20 (t, 1 H, J=3.9 Hz), 3.70 -3.82 (m, 2H), 3.39-3.45 (m, 1H), 3.09-3.15 (dd, 1 H, J=11.85 & 4.35 Hz).
Statistics shows that 764659-72-5 is playing an increasingly important role. we look forward to future research findings about (2R,5S)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate.
Reference:
Patent; MATRIX LABORATORIES LTD.; RAMA, Shankar; GORANTLA, Sarat, Chandra, Srikanth; VADALI, Lakshmana, Rao; INUPAKUTIKA, Venkata, Bala, Kishore, Sarma; DASARI, Srinivas, Rao; MITTAPELLY, Nagaraju; SINGH, Santosh, Kumar; DATTA, Debashish; WO2011/95987; (2011); A1;,
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