Propanamide, N-(4-bromophenyl)-3-[[[(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1 ]hept-1-yl]methyl]thio]-2-methyl-, (2R)-

Base Information

• Chemical Name: Propanamide, N-(4-bromophenyl)-3-[[[(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1 ]hept-1-yl]methyl]thio]-2-methyl-, (2R)-
• CAS No.: 370570-10-8
• Molecular Formula: C20H28BrNO2S
• Molecular Weight: 426.418
• Mol file: 370570-10-8.mol

Synonyms:

Chemical Property of Propanamide, N-(4-bromophenyl)-3-[[[(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1 ]hept-1-yl]methyl]thio]-2-methyl-, (2R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Propanamide, N-(4-bromophenyl)-3-[[[(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1 ]hept-1-yl]methyl]thio]-2-methyl-, (2R)-

There total 4 articles about Propanamide, N-(4-bromophenyl)-3-[[[(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1 ]hept-1-yl]methyl]thio]-2-methyl-, (2R)- 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:

N-(4-bromophenyl)methacrylamide (7600-35-3) + (1S,2R,4R)-(-)-10-mercaptoisoboneol (71242-58-5) → (R)-N-(4-Bromo-phenyl)-3-((1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-2-methyl-propionamide (370570-10-8) + (S)-N-(4-Bromo-phenyl)-3-((1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-2-methyl-propionamide

Guidance literature:

With dimethylaluminum chloride; In dichloromethane; at 20 ℃; for 1h; Title compound not separated from byproducts.;

DOI:10.1021/ol016406d

Reference yield:

(1S,2R,4R)-(-)-10-mercaptoisoboneol (71242-58-5) → (R)-N-(4-Bromo-phenyl)-3-((1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-2-methyl-propionamide (370570-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dimethylaluminum chloride / CH₂Cl₂; hexane / 0.12 h / 0 °C

1.2: CH₂Cl₂; hexane / 1 h / 20 °C

2.1: 93 percent / Me₂AlCl; 1-dodecyl methyl sulfide / 10 h / 0 - 20 °C

3.1: EDC; HOBt

With dodecyl methyl sulfide; dimethylaluminum chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In hexane; dichloromethane; 1.1: Michael addition / 1.2: Michael addition;

DOI:10.1021/ol016406d

Reference yield:

(2R)-benzyl 3-[(1S,2R,4R)-2-hydroxybornane-10-sulfenyl]-2-methylpropionate (370570-02-8) → (R)-N-(4-Bromo-phenyl)-3-((1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-2-methyl-propionamide (370570-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Me₂AlCl; 1-dodecyl methyl sulfide / 10 h / 0 - 20 °C

2: EDC; HOBt

With dodecyl methyl sulfide; dimethylaluminum chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide;

DOI:10.1021/ol016406d

upstream raw materials:

N-(4-bromophenyl)methacrylamide

(1S,2R,4R)-(-)-10-mercaptoisoboneol

4-bromo-aniline

(R)-3-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-2-methyl-propionic acid