Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate synthesis
- Product Name:Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate
- CAS Number:1206102-08-0
- Molecular formula:C16H17NO6
- Molecular Weight:319.31
1206102-07-9
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1206102-08-0
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Yield: 90%
Reaction Conditions:
with sodium periodate;sulfuric acid in water;acetonitrile at 14 - 17; for 1 h;Product distribution / selectivity;
Steps:
3g
To a mixture of 15.O g of compound 7(1.0 eq.) in 70.9 g of MeCN, a mixture of 60 mL ofH2O, 2.6 g of H2SO4 and 11.5 g of NaIO4 was added in the range between 17 0C to 140C. After the reaction mixture was stirred for 1 hour, precipitate was filtered. The filterate was added to the solution of 11.8 g of ascorbic acid sodium salt, 64 g of water and 60mg of H2SO4. After the mixture was concentrated, cooling to 5 0C, filtration, washing with H2O and drying provided 12.9 g of compound 8 (90% yield) as a crystal.1H NMR(300 MHz, DMSO-d6) δ 7.62 (d, J = 7.5 Hz, 1 H), 7.42-7.30 (m, 5H), 6.33 (d, J = 6.0 Hz, 2H), 6.29 (d, J = 7.5 Hz, 1H), 5.08 (s, 2H), 4.95-4.85 (m, 1H), 3.80 (s, 3H), 3.74 (d, J = 5.1 Hz, 2H).
References:
GLAXOSMITHKLINE LLC;SHIONOGI & CO., LTD.;JOHNS, Brian, Alvin;DUAN, Maosheng;HAKOGI, Toshikazu WO2010/68262, 2010, A1 Location in patent:Page/Page column 23
119736-16-2
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1206102-08-0
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118-71-8
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1206102-08-0
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100-39-0
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1206102-08-0
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61049-69-2
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1206102-08-0
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