(3R,5S)-1-(tert-butoxycarbonyl)-5-[{[3-(4-methoxybutyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid

Base Information

• Chemical Name: (3R,5S)-1-(tert-butoxycarbonyl)-5-[{[3-(4-methoxybutyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid
• CAS No.: 1202263-06-6
• Molecular Formula: C₂₈H₄₂N₄O₆
• Molecular Weight: 530.665
• Mol file: 1202263-06-6.mol

Synonyms:

Chemical Property of (3R,5S)-1-(tert-butoxycarbonyl)-5-[{[3-(4-methoxybutyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-1-(tert-butoxycarbonyl)-5-[{[3-(4-methoxybutyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid

There total 11 articles about (3R,5S)-1-(tert-butoxycarbonyl)-5-[{[3-(4-methoxybutyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid 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: 100.0%

1-tert-butyl 3-methyl (3R,5S)-5-[{[3-(4-methoxybutyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-1,3-dicarboxylate → (3R,5S)-1-(tert-butoxycarbonyl)-5-[{[3-(4-methoxybutyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid (1202263-06-6)

Guidance literature:

With sodium hydroxide; In methanol; water; at 60 ℃; for 2h;

DOI:10.1016/j.bmc.2018.04.051

Reference yield:

1-(tert-butoxycarbonyl)piperidine-3,5-dicarboxylic acid (920297-39-8) → (3R,5S)-1-(tert-butoxycarbonyl)-5-[{[3-(4-methoxybutyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid (1202263-06-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetic anhydride / 3 h / Reflux

2.1: hydroquinidine (anthraquinone-1,4-diyl) diether / methanol; diethyl ether; tetrahydrofuran / 24 h / -40 °C / Inert atmosphere

3.1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 100 °C

4.1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 16 h / 20 °C

5.1: lithium hydroxide monohydrate / ethanol / 15 h / 60 °C

5.2: 15 h / 20 °C

6.1: sodium hydroxide / methanol; water / 2 h / 60 °C

With lithium hydroxide monohydrate; diphenyl phosphoryl azide; 10 wt% Pd(OH)2 on carbon; hydrogen; acetic anhydride; triethylamine; sodium hydroxide; hydroquinidine (anthraquinone-1,4-diyl) diether; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; toluene;

DOI:10.1016/j.bmc.2018.04.051

Reference yield:

2,4-dioxo-3-oxa-7-azabicyclo[3.3.1]nonane-7-carboxylic acid tert-butyl ester (914260-44-9) → (3R,5S)-1-(tert-butoxycarbonyl)-5-[{[3-(4-methoxybutyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid (1202263-06-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: quinidine / methanol; tetrahydrofuran / 7 h / -40 °C

2.1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 100 °C

3.1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 16 h / 20 °C

4.1: lithium hydroxide monohydrate / ethanol / 15 h / 60 °C

4.2: 15 h / 20 °C

5.1: sodium hydroxide / methanol; water / 2 h / 60 °C

With lithium hydroxide monohydrate; diphenyl phosphoryl azide; 10 wt% Pd(OH)2 on carbon; hydrogen; triethylamine; sodium hydroxide; quinidine; In tetrahydrofuran; methanol; ethanol; water; toluene;

DOI:10.1016/j.bmc.2018.04.051

upstream raw materials:

1-(tert-butoxycarbonyl)piperidine-3,5-dicarboxylic acid

2,4-dioxo-3-oxa-7-azabicyclo[3.3.1]nonane-7-carboxylic acid tert-butyl ester

1-tert-butyl 3-methyl (3R,5S)-5-{[(benzyloxy)carbonyl]amino}piperidine-1,3-dicarboxylate

1-tert-butyl 3-methyl (3R,5S)-5-[(2-methylpropyl)amino]piperidine-1,3-dicarboxylate