Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate

Base Information

• Chemical Name: Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate
• CAS No.: 1206102-08-0
• Molecular Formula: C16H17NO6
• Molecular Weight: 319.314
• Mol file: 1206102-08-0.mol

Synonyms:Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate;methyl 3-(benzyloxy)-1,4-dihydro-1-(2,2-dihydroxyethyl)-4-oxopyridine-2-carboxylate;Methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate

Chemical Property of Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate

Chemical Property:

• Boiling Point: 542.7±50.0 °C(Predicted)
• PKA: 12.54±0.41(Predicted)
• PSA: 97.99000
• Density: 1.38±0.1 g/cm3(Predicted)
• LogP: 0.52460

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate

There total 11 articles about Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester (1206102-07-9) → methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate (1206102-08-0)

Guidance literature:

With sodium periodate; sulfuric acid; In water; acetonitrile; at 14 - 17 ℃; for 1h; Product distribution / selectivity;

Reference yield:

3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester (119736-16-2) → methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate (1206102-08-0)

Guidance literature:

Multi-step reaction with 3 steps

1: ethanol / Inert atmosphere; Reflux

2: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one / 20 °C / Inert atmosphere

3: sodium periodate; acetic acid / acetonitrile; water / 2 h / 20 °C

With sodium periodate; sodium hydrogencarbonate; acetic acid; In 1-methyl-pyrrolidin-2-one; ethanol; water; acetonitrile;

Reference yield:

Maltol (118-71-8) → methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate (1206102-08-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium carbonate / acetonitrile / Inert atmosphere; Reflux; Large scale

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -60 °C / Inert atmosphere

2.2: 2 h / -60 °C / Inert atmosphere

3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 2 h / -30 °C / Inert atmosphere

3.2: 0.33 h / 0 °C

4.1: ruthenium trichloride; sodium periodate / acetonitrile; ethyl acetate; water / 2 h / 15 °C / Inert atmosphere

4.2: 2 h / 20 °C

5.1: ethanol / Inert atmosphere; Reflux

6.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one / 20 °C / Inert atmosphere

7.1: sodium periodate; acetic acid / acetonitrile; water / 2 h / 20 °C

With ruthenium trichloride; sodium periodate; sodium hydrogencarbonate; potassium carbonate; acetic acid; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; water; ethyl acetate; acetonitrile;

upstream raw materials:

1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester

3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester

1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid

Maltol

Refernces

• 1、 Yasukata, Tatsuro,Masui, Moriyasu,Ikarashi, Fumiya,Okamoto, Kazuya,Kurita, Takanori,Nagai, Masahiko,Sugata, Yoshihide,Miyake, Naoki,Hara, Shinichiro,Adachi, You,Sumino, Yukihito. "Practical Synthetic Method for the Preparation of Pyrone Diesters: An Efficient Synthetic Route for the Synthesis of Dolutegravir Sodium". . p. 565 - 570. Retrieved 2019/03/26.
• 2、 -. "Intermediate of these pyridonecarboxylic carbamoylalkanoic and HIV integrase inhibitor". Paragraph 0039. . Retrieved 2016/10/07.