(R)-[1-(2-{4-[3-(2,3-dichloro-4-triisopropylsilanyloxy-phenyl)-3-oxo-prop-1-ynyl]-piperidin-1-yl}-2-oxo-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: (R)-[1-(2-{4-[3-(2,3-dichloro-4-triisopropylsilanyloxy-phenyl)-3-oxo-prop-1-ynyl]-piperidin-1-yl}-2-oxo-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester
• CAS No.: 515846-33-0
• Molecular Formula: C₃₆H₅₅Cl₂N₃O₆Si
• Molecular Weight: 724.841
• Mol file: 515846-33-0.mol

Synonyms:(R)-[1-(2-{4-[3-(2,3-dichloro-4-triisopropylsilanyloxy-phenyl)-3-oxo-prop-1-ynyl]-piperidin-1-yl}-2-oxo-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

Chemical Property of (R)-[1-(2-{4-[3-(2,3-dichloro-4-triisopropylsilanyloxy-phenyl)-3-oxo-prop-1-ynyl]-piperidin-1-yl}-2-oxo-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-[1-(2-{4-[3-(2,3-dichloro-4-triisopropylsilanyloxy-phenyl)-3-oxo-prop-1-ynyl]-piperidin-1-yl}-2-oxo-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

There total 13 articles about (R)-[1-(2-{4-[3-(2,3-dichloro-4-triisopropylsilanyloxy-phenyl)-3-oxo-prop-1-ynyl]-piperidin-1-yl}-2-oxo-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester 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-dichloro-4-triisopropylsilanyloxy-benzoyl chloride (515846-31-8) + (R)-{1-[2-(4-ethynyl-piperidin-1-yl)-2-oxo-ethylcarbamoyl]-3-methyl-butyl}carbamic acid tert-butyl ester (515846-24-9) → (R)-[1-(2-{4-[3-(2,3-dichloro-4-triisopropylsilanyloxy-phenyl)-3-oxo-prop-1-ynyl]-piperidin-1-yl}-2-oxo-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester (515846-33-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In toluene; at 20 ℃;

DOI:10.1021/ja034247i

Reference yield:

2,3-dichlorophenol (576-24-9) → (R)-[1-(2-{4-[3-(2,3-dichloro-4-triisopropylsilanyloxy-phenyl)-3-oxo-prop-1-ynyl]-piperidin-1-yl}-2-oxo-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester (515846-33-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 53 percent / bromine / CH₂Cl₂ / 2 h

2.1: triethylamine / tetrahydrofuran / 1 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: 6.65 g / tetrahydrofuran; hexane / -78 - 20 °C

4.1: oxalyl chloride; DMF / CH₂Cl₂ / 0.17 h

5.1: CuI; PdCl₂(PPh₃)2; triethylamine / toluene

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; oxalyl dichloride; bromine; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; hexane; dichloromethane; toluene; 5.1: Mitsunobu reaction;

DOI:10.1021/jm049967u

Reference yield:

4-bromo-2,3-dichlorophenol (1940-44-9) → (R)-[1-(2-{4-[3-(2,3-dichloro-4-triisopropylsilanyloxy-phenyl)-3-oxo-prop-1-ynyl]-piperidin-1-yl}-2-oxo-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester (515846-33-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / tetrahydrofuran / 1 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

2.2: 6.65 g / tetrahydrofuran; hexane / -78 - 20 °C

3.1: oxalyl chloride; DMF / CH₂Cl₂ / 0.17 h

4.1: CuI; PdCl₂(PPh₃)2; triethylamine / toluene

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; hexane; dichloromethane; toluene; 4.1: Mitsunobu reaction;

DOI:10.1021/jm049967u

upstream raw materials:

2,3-dichloro-4-triisopropylsilanyloxy-benzoyl chloride

(R)-{1-[2-(4-ethynyl-piperidin-1-yl)-2-oxo-ethylcarbamoyl]-3-methyl-butyl}carbamic acid tert-butyl ester

triisopropylsilyl chloride

2,3-dichlorophenol

Downstream raw materials:

(R)-[1-(2-{4-[5-(2,3-dichloro-4-triisopropylsilanyloxy-phenyl)-2-methyl-2H-pyrazol-3-yl]-piperidin-1-yl}-2-oxo-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

(R)-[1-(2-{4-[5-(2,3-dichloro-4-hydroxy-phenyl)-2-methyl-2H-pyrazol-3-yl]-piperidin-1-yl}-2-oxo-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

(R)-5-[4-(5-{1-[2-(2-tert-butoxycarbonylamino-4-methyl-pentanoylamino)acetyl]-piperidin-4-yl}-1-methyl-1H-pyrazol-3-yl)-2,3-dichloro-phenoxymethyl]furan-2-carboxylic acid methyl ester

(R)-3-[4-(5-{1-[2-(2-tert-butoxycarbonylamino-4-methyl-pentanoylamino)acetyl]-piperidin-4-yl}-1-methyl-1H-pyrazol-3-yl)-2,3-dichloro-phenoxymethyl]benzoic acid