3-Pyridinecarboxylic acid, 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(2-fluorophenyl)-2-hydroxy butyl]-

Base Information

• Chemical Name: 3-Pyridinecarboxylic acid, 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(2-fluorophenyl)-2-hydroxy butyl]-
• CAS No.: 923563-66-0
• Molecular Formula: C21H25FN2O5
• Molecular Weight: 404.438
• Mol file: 923563-66-0.mol

Synonyms:

Chemical Property of 3-Pyridinecarboxylic acid, 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(2-fluorophenyl)-2-hydroxy butyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Pyridinecarboxylic acid, 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(2-fluorophenyl)-2-hydroxy butyl]-

There total 2 articles about 3-Pyridinecarboxylic acid, 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(2-fluorophenyl)-2-hydroxy butyl]- 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:

2-[3-tert-butoxycarbonylamino-4-(2-fluoro-phenyl)-2-oxo-butyl]-nicotinic acid (923563-65-9) → 2-[3-tert-butoxycarbonylamino-4-(2-fluoro-phenyl)-2-hydroxy-butyl]-nicotinic acid (923563-66-0)

Guidance literature:

2-[3-tert-butoxycarbonylamino-4-(2-fluoro-phenyl)-2-oxo-butyl]-nicotinic acid; With sodium tetrahydroborate; In ethanol; at 0 ℃; for 0.333333h;

With sodium hydrogen sulfate; water; In ethanol; pH=~ 3;

Reference yield:

[2-(2-fluoro-phenyl)-1-(methoxymethyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester (923564-33-4) → 2-[3-tert-butoxycarbonylamino-4-(2-fluoro-phenyl)-2-hydroxy-butyl]-nicotinic acid (923563-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.67 h / -68 - -40 °C

1.2: 1.17 h / -68 °C

2.1: sodium tetrahydroborate / ethanol / 0.33 h / 0 °C

2.2: pH ~ 3

With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide; In tetrahydrofuran; ethanol; n-heptane; ethylbenzene;

Reference yield:

2-[3-tert-butoxycarbonylamino-4-(2-fluoro-phenyl)-2-hydroxy-butyl]-nicotinic acid (923563-66-0) → 2-[3-tert-butoxycarbonyl-4-(2-fluoro-benzyl)-2,2-dimethyl-oxazolidin-5-ylmethyl]-nicotinic acid

Guidance literature:

With boron trifluoride diethyl etherate; In 2,2-dimethoxy-propane; acetone; at 0 - 40 ℃;

upstream raw materials:

2-[3-tert-butoxycarbonylamino-4-(2-fluoro-phenyl)-2-oxo-butyl]-nicotinic acid

[2-(2-fluoro-phenyl)-1-(methoxymethyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester

Downstream raw materials:

2-[(4R,5S)-3-tert-butoxycarbonyl-4-(2-fluoro-benzyl)-2,2-dimethyl-oxazolidin-5-ylmethyl]-nicotinic acid methyl ester

2-[(4R,5S)-3-tert-butoxycarbonyl-4-(2-fluoro-benzyl)-2,2-dimethyl-oxazolidin-5-ylmethyl]-nicotinic acid

(4R,5S)-4-(2-fluoro-benzyl)-2,2-dimethyl-5-(3-methylcarbamoyl-pyridin-2-ylmethyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Refernces