(4R)-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2,5,5-trimethyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a][2,6]naphthyridine-1,8,10(11H)-trione

Base Information

Chemical Name:(4R)-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2,5,5-trimethyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a][2,6]naphthyridine-1,8,10(11H)-trione
CAS No.:1019339-38-8
Molecular Formula:C₂₉H₃₅ClFN₃O₆
Molecular Weight:576.065
Hs Code.:

(4R)-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2,5,5-trimethyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a][2,6]naphthyridine-1,8,10(11H)-trione

Synonyms:(4R)-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2,5,5-trimethyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a][2,6]naphthyridine-1,8,10(11H)-trione

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Chemical Property of (4R)-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2,5,5-trimethyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a][2,6]naphthyridine-1,8,10(11H)-trione

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Technology Process of (4R)-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2,5,5-trimethyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a][2,6]naphthyridine-1,8,10(11H)-trione

There total 26 articles about (4R)-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2,5,5-trimethyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a][2,6]naphthyridine-1,8,10(11H)-trione 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:

: 1080623-44-4
methanesulfonic acid (R)-4-{[6-(3-chloro-4-fluorobenzyl)-3-methanesulfonyloxy-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carbonyl]-methyl-amino}-2,2-dimethyl-3-(tetrahydropyran-2-yloxy)-butyl ester

: 1019339-38-8
(4R)-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2,5,5-trimethyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a][2,6]naphthyridine-1,8,10(11H)-trione

Guidance literature:: methanesulfonic acid (R)-4-{[6-(3-chloro-4-fluorobenzyl)-3-methanesulfonyloxy-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carbonyl]-methyl-amino}-2,2-dimethyl-3-(tetrahydropyran-2-yloxy)-butyl ester; With caesium carbonate; In N,N-dimethyl acetamide; at 105 ℃; for 7h; Large scale;

With water; In N,N-dimethyl acetamide; at 20 ℃; for 16h; Large scale;
DOI:10.1021/acs.joc.6b01229

Reference yield:

: C₃₀H₃₉ClFN₃O₉S

: 1080623-44-4
methanesulfonic acid (R)-4-{[6-(3-chloro-4-fluorobenzyl)-3-methanesulfonyloxy-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carbonyl]-methyl-amino}-2,2-dimethyl-3-(tetrahydropyran-2-yloxy)-butyl ester

: 1019339-38-8
(4R)-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2,5,5-trimethyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a][2,6]naphthyridine-1,8,10(11H)-trione

Guidance literature:: With caesium carbonate; In N,N-dimethyl-formamide; at 150 ℃; for 0.5h; Product distribution / selectivity; Microwave irradiation;

Reference yield:

: 599-04-2
(R)-Pantolacton

: 1019339-38-8
(4R)-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2,5,5-trimethyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a][2,6]naphthyridine-1,8,10(11H)-trione

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / dichloromethane / 1.5 h / -5 - 20 °C / Large scale

2.1: ethanol / 18 h / 20 °C

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4.75 h / -5 - 90 °C / Large scale

4.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / N,N-dimethyl-formamide / 20 °C / Large scale

5.1: potassium tert-butylate / tetrahydrofuran; toluene / 1 h / 10 - 15 °C

5.2: 1 h / 10 - 15 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 95 °C

With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; potassium tert-butylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/acs.joc.6b01229