ethyl 7-<(1R,4R,7S)-7-methyl-5-phenylmethyl-2,5-diazabicyclo<2.2.1>heptan-2-yl>-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Base Information

• Chemical Name: ethyl 7-<(1R,4R,7S)-7-methyl-5-phenylmethyl-2,5-diazabicyclo<2.2.1>heptan-2-yl>-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate
• CAS No.: 153061-77-9
• Molecular Formula: C₂₈H₃₃FN₄O₃
• Molecular Weight: 492.593
• Mol file: 153061-77-9.mol

Synonyms:ethyl 7-<(1R,4R,7S)-7-methyl-5-phenylmethyl-2,5-diazabicyclo<2.2.1>heptan-2-yl>-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Chemical Property of ethyl 7-<(1R,4R,7S)-7-methyl-5-phenylmethyl-2,5-diazabicyclo<2.2.1>heptan-2-yl>-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 7-<(1R,4R,7S)-7-methyl-5-phenylmethyl-2,5-diazabicyclo<2.2.1>heptan-2-yl>-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

There total 6 articles about ethyl 7-<(1R,4R,7S)-7-methyl-5-phenylmethyl-2,5-diazabicyclo<2.2.1>heptan-2-yl>-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-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: 72.0%

1-(1,1-dimethylethyl)-1,4-dihydro-6-fluoro-7-chloro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester (116163-18-9) + (1R,4R,7R)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane dihydrobromide → ethyl 7-<(1R,4R,7S)-7-methyl-5-phenylmethyl-2,5-diazabicyclo<2.2.1>heptan-2-yl>-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (153061-77-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 4h; Heating;

DOI:10.1016/0223-5234(93)90013-5

Reference yield:

(1R,4R,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane (153061-75-7) → ethyl 7-<(1R,4R,7S)-7-methyl-5-phenylmethyl-2,5-diazabicyclo<2.2.1>heptan-2-yl>-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (153061-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 33percent HBr / acetic acid / 24 h / 70 °C

2: 72 percent / DBU / acetonitrile / 4 h / Heating

With hydrogen bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetic acid; acetonitrile;

DOI:10.1016/0223-5234(93)90013-5

Reference yield:

ethyl (2R,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine (152955-42-5) → ethyl 7-<(1R,4R,7S)-7-methyl-5-phenylmethyl-2,5-diazabicyclo<2.2.1>heptan-2-yl>-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (153061-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / pyridine / Ambient temperature

2: 86 percent / xylene / 12 h / Heating

3: 33percent HBr / acetic acid / 24 h / 70 °C

4: 72 percent / DBU / acetonitrile / 4 h / Heating

With pyridine; hydrogen bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetic acid; acetonitrile; xylene;

DOI:10.1016/0223-5234(93)90013-5

upstream raw materials:

1-(1,1-dimethylethyl)-1,4-dihydro-6-fluoro-7-chloro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester

ethyl (2R,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine

(1R,4R,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane

(2R,3R,4S)-1-(4-toluenesulfonyl)-2-(4-toluenesulfonyloxymethyl)-3-methyl-4-(4-toluenesulfonyloxy)pyrrolidine