3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

Base Information

• Chemical Name: 3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid
• CAS No.: 1206102-06-8
• Molecular Formula: C₁₆H₁₇NO₆
• Molecular Weight: 319.314
• Mol file: 1206102-06-8.mol

Synonyms:3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid;1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid

Chemical Property of 3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

Chemical Property:

• Solubility.: DCM, DMSO, Methanol

Purity/Quality:

98.5% ^*data from raw suppliers

1-(2,3-Dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1-(2,3-Dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic Acid is an intermediate in the synthesis of Dolutegravir (D528800), a second generation HIV-1 integrase strand transfer inhibitor.

Technology Process of 3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

There total 11 articles about 3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid 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: 85.0%

3-Amino-1,2-propanediol (616-30-8,13552-31-3,98923-21-8) + 3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester (119736-16-2) → 1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid (1206102-06-8)

Guidance literature:

In ethanol; for 1h; Reflux;

Reference yield:

Maltol (118-71-8) → 1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid (1206102-06-8)

Guidance literature:

Multi-step reaction with 5 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

With ruthenium trichloride; sodium periodate; potassium carbonate; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; acetonitrile;

Reference yield:

2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one (1206102-04-6) → 1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid (1206102-06-8)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 0.33 h / 0 °C

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

2.2: 2 h / 20 °C

3.1: ethanol / Inert atmosphere; Reflux

With ruthenium trichloride; sodium periodate; methanesulfonyl chloride; triethylamine; In ethanol; dichloromethane; water; ethyl acetate; acetonitrile;

upstream raw materials:

3-Amino-1,2-propanediol

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

Maltol

benzyl bromide

Downstream raw materials:

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

methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate

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 0032; 0038. . Retrieved 2016/10/07.