1-(S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-methylprop-1-yl]-6-(3-chloro-2-fluorobenzyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Base Information

• Chemical Name: 1-(S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-methylprop-1-yl]-6-(3-chloro-2-fluorobenzyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• CAS No.: 1261283-99-1
• Molecular Formula: C₂₉H₃₇ClFNO₅Si
• Molecular Weight: 562.153
• Mol file: 1261283-99-1.mol

Synonyms:1-(S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-methylprop-1-yl]-6-(3-chloro-2-fluorobenzyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property of 1-(S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-methylprop-1-yl]-6-(3-chloro-2-fluorobenzyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-methylprop-1-yl]-6-(3-chloro-2-fluorobenzyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

There total 15 articles about 1-(S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-methylprop-1-yl]-6-(3-chloro-2-fluorobenzyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-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:

elvitegravir (697761-98-1) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-(S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-methylprop-1-yl]-6-(3-chloro-2-fluorobenzyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1261283-99-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 3h;

Reference yield:

2,4-difluoro-benzoic acid (1583-58-0) → 1-(S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-methylprop-1-yl]-6-(3-chloro-2-fluorobenzyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1261283-99-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sulfuric acid / dichloromethane / 0.5 h / 0 - 5 °C

1.2: 5 °C

2.1: thionyl chloride / N,N-dimethyl-formamide; toluene / 85 - 90 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / toluene / 4.5 h / 90 - 95 °C

4.1: toluene / 1.5 h / 20 °C / Cooling

5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

6.1: 1H-imidazole / dichloromethane

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 6 h / 40 °C / Inert atmosphere

8.1: sodium hydroxide; water / 55 °C

8.2: 10 - 15 °C / pH 3 - 3.5

9.1: water; methanol / 20 °C / Inert atmosphere; Reflux

10.1: hydrogenchloride / ethyl acetate; water / 10 - 15 °C / pH 3 - 8.5

11.1: 1H-imidazole / dichloromethane / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; thionyl chloride; sulfuric acid; water; potassium carbonate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

Reference yield:

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) → 1-(S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-methylprop-1-yl]-6-(3-chloro-2-fluorobenzyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1261283-99-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 0.25 h

1.2: 0 - 20 °C

2.1: toluene / 1.5 h / 20 °C / Cooling

3.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

4.1: 1H-imidazole / dichloromethane

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 6 h / 40 °C / Inert atmosphere

6.1: sodium hydroxide; water / 55 °C

6.2: 10 - 15 °C / pH 3 - 3.5

7.1: water; methanol / 20 °C / Inert atmosphere; Reflux

8.1: hydrogenchloride / ethyl acetate; water / 10 - 15 °C / pH 3 - 8.5

9.1: 1H-imidazole / dichloromethane / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; water; potassium carbonate; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

upstream raw materials:

2,4-difluoro-benzoic acid

elvitegravir

tert-butyldimethylsilyl chloride

(S)-valinol