methyl 3-(benzyloxy)-5-((4-fluorobengzyl)carbamoyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate

Base Information

• Chemical Name: methyl 3-(benzyloxy)-5-((4-fluorobengzyl)carbamoyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate
• CAS No.: 906657-98-5
• Molecular Formula: C₂₄H₂₁FN₂O₆
• Molecular Weight: 452.439
• Mol file: 906657-98-5.mol

Synonyms:methyl 3-(benzyloxy)-5-((4-fluorobengzyl)carbamoyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate

Chemical Property of methyl 3-(benzyloxy)-5-((4-fluorobengzyl)carbamoyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-(benzyloxy)-5-((4-fluorobengzyl)carbamoyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate

There total 21 articles about methyl 3-(benzyloxy)-5-((4-fluorobengzyl)carbamoyl)-4-oxo-1-(2-oxoethyl)-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: 71.0%

methyl 1-allyl-3-benzyloxy-5-(4-fluorobenzylcarbamoyl)-4-oxo-1,4-dihydropyridine-2-carboxylate (906657-97-4) → methyl 3-(benzyloxy)-5-((4-fluorobengzyl)carbamoyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate (906657-98-5)

Guidance literature:

With potassium osmate(VI) dihydrate; sodium periodate; In 1,4-dioxane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm301550c

Reference yield:

benzyl bromide (100-39-0) → methyl 3-(benzyloxy)-5-((4-fluorobengzyl)carbamoyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate (906657-98-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 1.25 h / 80 °C / Inert atmosphere

2.1: ammonia; sodium hydroxide / ethanol / 1 h / 90 °C / Inert atmosphere

3.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C / Inert atmosphere

4.1: palladium diacetate; triethylamine; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C / Inert atmosphere

5.1: 0.67 h / 130 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 20 °C / Inert atmosphere; Cooling with ice

7.1: 0.33 h / 130 °C / Inert atmosphere

8.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice

9.1: N,N-dimethyl-formamide / 1.5 h / 120 °C / Inert atmosphere

10.1: manganese(IV) oxide / chloroform / 1 h / 20 °C / Inert atmosphere

11.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran; water / 1 h / 20 °C / Inert atmosphere; Cooling with ice

12.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere

12.2: 1.5 h / Inert atmosphere; Reflux

13.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C / Inert atmosphere

14.1: potassium osmate(VI) dihydrate; sodium periodate / 1,4-dioxane / 2 h / 20 °C / Inert atmosphere

With manganese(IV) oxide; potassium osmate(VI) dihydrate; sodium chlorite; sodium periodate; N-Bromosuccinimide; 1,3-bis-(diphenylphosphino)propane; aminosulfonic acid; ammonia; sodium methylate; palladium diacetate; potassium carbonate; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm301550c

Reference yield:

3-O-benzylmaltol (61049-69-2) → methyl 3-(benzyloxy)-5-((4-fluorobengzyl)carbamoyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate (906657-98-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: ammonia; sodium hydroxide / ethanol / 1 h / 90 °C / Inert atmosphere

2.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C / Inert atmosphere

3.1: palladium diacetate; triethylamine; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 18.5 h / 20 - 80 °C / Inert atmosphere

4.1: 0.67 h / 130 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / 20 °C / Inert atmosphere; Cooling with ice

6.1: 0.33 h / 130 °C / Inert atmosphere

7.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice

8.1: N,N-dimethyl-formamide / 1.5 h / 120 °C / Inert atmosphere

9.1: manganese(IV) oxide / chloroform / 1 h / 20 °C / Inert atmosphere

10.1: sodium chlorite; aminosulfonic acid / tetrahydrofuran; water / 1 h / 20 °C / Inert atmosphere; Cooling with ice

11.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere

11.2: 1.5 h / Inert atmosphere; Reflux

12.1: caesium carbonate / N,N-dimethyl-formamide / 4.5 h / 20 °C / Inert atmosphere

13.1: potassium osmate(VI) dihydrate; sodium periodate / 1,4-dioxane / 2 h / 20 °C / Inert atmosphere

With manganese(IV) oxide; potassium osmate(VI) dihydrate; sodium chlorite; sodium periodate; N-Bromosuccinimide; 1,3-bis-(diphenylphosphino)propane; aminosulfonic acid; ammonia; sodium methylate; palladium diacetate; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm301550c

upstream raw materials:

methyl 1-allyl-3-benzyloxy-5-(4-fluorobenzylcarbamoyl)-4-oxo-1,4-dihydropyridine-2-carboxylate

5-benzyloxy-N-(4-fluorobenzyl)-6-formyl-4-oxo-1,4-dihydropyridine-3-carboxamide

3-benzyloxy-5-(4-fluorobenzylcarbamoyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid

methyl 3-benzyloxy-5-(4-fluorobenzylcarbamoyl)-4-oxo-1,4-dihydropyridine-2-carboxylate

Downstream raw materials:

9-benzyloxy-2-(2-methoxyethyl)-1,8-dioxo-1,8-dihydro-2H-pyrid[1,2-a]pyrazine-7-carboxylic acid 4-fluorobenzylamide

7-(benzyloxy)-N-(4-fluorobenzyl)-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1′,2′:4,5]pyrazino[2,1-b][1,3]-oxazine-9-carboxamide

1-benzyloxy-2,11-dioxo-2,5,5a,7,8,9,10,11-octahydro-6-oxa-4a,10a-diazacyclohepta[b]naphthalene-3-carboxylic acid 4-fluorobenzylamide

6-benzyloxy-N-(4-fluorobenzyl)-1-isopropyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro-1H-imidazo[1,2-d]pyrido[1,2-a]-pyrazine-8-carboxamide