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

Product Name: Methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate
CAS No.: 1206102-07-9
Chemical Name: Methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate
Synonyms: Methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate;3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid methyl ester;2-Pyridinecarboxylic acid, 1-(2,3-dihydroxypropyl)-1,4-dihydro-4-oxo-3-(phenylmethoxy)-, methyl ester;1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester
CBNumber: CB32703782
Molecular Formula: C17H19NO6
Formula Weight: 333.34
MOL File: 1206102-07-9.mol

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

storage temp.: Sealed in dry,Room Temperature
form: Solid
color: White

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: D454660
Product name: 1-(2,3-Dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylicAcidMethylEster
Packaging: 10mg
Price: $140
Updated: 2021/12/16

AK Scientific

Product number: 9754DN
Product name: Methyl3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate
Packaging: 1g
Price: $109
Updated: 2021/12/16

AK Scientific

Product number: 9754DN
Product name: Methyl3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate
Packaging: 5g
Price: $226
Updated: 2021/12/16

Ambeed

Product number: A308180
Product name: Methyl3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate
Purity: 97%
Packaging: 250mg
Price: $23
Updated: 2021/12/16

Ambeed

Product number: A308180
Product name: Methyl3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate
Purity: 97%
Packaging: 1g
Price: $49
Updated: 2021/12/16

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Methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate Chemical Properties,Usage,Production

Uses

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

Synthesis

1206102-06-8

77-78-1

1206102-07-9

GENERAL STEPS: 3-(Benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid (4.302 kg, 13.47 mol) was added to the reactor, followed by sodium bicarbonate (1.69 kg, 20.09 mol) and deionized water (242 g). N-methylpyrrolidone (21.4 kg) was added to the mixture, stirred and warmed up to 28-35 °C. Dimethyl sulfate (2.34 kg, 18.30 mol) was added slowly and dropwise through the addition funnel over a period of 1-3 h. The reaction temperature was maintained at 28-33°C. Stirring of the reaction mixture was continued at this temperature for 14 hours. Upon completion of the reaction, the mixture was cooled to below 5 °C and neutralized with aqueous hydrochloric acid (561 mL of concentrated hydrochloric acid dissolved in 2806 g of deionized water) to pH 6. A pre-cooled 20% brine solution (consisting of 8.7 kg of sodium chloride, 20 kg of deionized water, and 14.8 kg of ice) was slowly added to the reaction vessel to a controlled temperature of no more than 100 °C. The reaction was carried out at a temperature of 0-100 °C. The reaction temperature was controlled at 0-100 °C. The mixture was stirred at 0-100°C for 2.5 hours. After completion of the reaction, the slurry was vacuum filtered and the filter cake was washed twice with deionized water (15 kg). The wet solid product was dried under vacuum at 45-55 °C to constant weight to afford the target product, methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate, as a light yellow solid (3.77 kg, 84% yield, 99.42% HPLC purity).1H NMR (300 MHz, DMSO-d6) δ 7.60 (d, J = 7.5 Hz, 1H), 7.36 (m, 5H), 6.28 (d, J = 7.5 Hz, 1H), 5.23 (d, J = 5.4 Hz, 1H), 5.10 (ABq, J = 10.8 Hz, 2H), 4.85 (m, 1H), 3.98 (dd, J = 14.3, 2.4 Hz, 1H), 3.79 (s, 3H), 3.70 (dd, J = 14.3, 9.0 Hz, 1H), 3.58 (m, 1H), 3.23 (m, 1H).

References

[1] Patent: WO2010/68262, 2010, A1. Location in patent: Page/Page column 31-32
[2] Patent: JP5848595, 2016, B2. Location in patent: Paragraph 0050

Methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate Preparation Products And Raw materials

Raw materials

Preparation Products

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

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View Lastest Price from Methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: Methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate 1206102-07-9
Price: US $0.00-0.00/Kg
Min. Order: 100G
Purity: 99.0%+
Supply Ability: 100 tons
Release date: 2020-01-16

Career Henan Chemical Co

Product: Methyl3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate 1206102-07-9
Price: US $1.00/g
Min. Order: 1g
Purity: 99%
Supply Ability: g/kg/T
Release date: 2019-12-18

1206102-07-9, Methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylateRelated Search:

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

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

2-Pyridinecarboxylic acid, 1-(2,3-dihydroxypropyl)-1,4-dihydro-4-oxo-3-(phenylmethoxy)-, methyl ester

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

1206102-07-9