2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2(S),3-dihydroxy-propoxy)-pyrazin-2-yl]-propionamide

Base Information

• Chemical Name: 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2(S),3-dihydroxy-propoxy)-pyrazin-2-yl]-propionamide
• CAS No.: 710321-71-4
• Molecular Formula: C₂₂H₂₈ClN₃O₆S
• Molecular Weight: 498
• Mol file: 710321-71-4.mol

Synonyms:2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2(S),3-dihydroxy-propoxy)-pyrazin-2-yl]-propionamide

Chemical Property of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2(S),3-dihydroxy-propoxy)-pyrazin-2-yl]-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2(S),3-dihydroxy-propoxy)-pyrazin-2-yl]-propionamide

There total 5 articles about 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2(S),3-dihydroxy-propoxy)-pyrazin-2-yl]-propionamide 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: 18.6%

N-(5-allyloxy-pyrazin-2-yl)-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (710322-75-1) → 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2(S),3-dihydroxy-propoxy)-pyrazin-2-yl]-propionamide (710321-71-4)

Guidance literature:

With hydroquinine 1,4-phthalazinediyl diether; potassium carbonate; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 25 ℃; for 0.0833333h;

N-(5-allyloxy-pyrazin-2-yl)-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide; With osmium(VIII) oxide; In water; toluene; tert-butyl alcohol; for 2.08333h;

Reference yield:

5-allyloxy-pyrazine-2-carboxylic acid potassium salt (710322-72-8) → 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2(S),3-dihydroxy-propoxy)-pyrazin-2-yl]-propionamide (710321-71-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diphenyl phosphoryl azide / N,N-dimethyl-formamide / 18 h / 25 °C / Inert atmosphere

1.2: Inert atmosphere; Reflux

2.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

3.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2.25 h / 0 - 25 °C / Inert atmosphere

3.2: 0 - 25 °C / Inert atmosphere

4.1: potassium hexacyanoferrate(III); potassium carbonate; osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / water; tert-butyl alcohol; toluene / 0 °C / Inert atmosphere

4.2: 0.5 h / Inert atmosphere

With osmium(VIII) oxide; oxalyl dichloride; diphenyl phosphoryl azide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; trifluoroacetic acid; potassium hexacyanoferrate(III); In dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/ml400027y

Reference yield:

(R)-2-(3-chloro-4-(methylsulfonyl)phenyl)-3-cyclopentylpropanoic acid (300356-14-3) → 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2(S),3-dihydroxy-propoxy)-pyrazin-2-yl]-propionamide (710321-71-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2.25 h / 0 - 25 °C / Inert atmosphere

1.2: 0 - 25 °C / Inert atmosphere

2.1: potassium hexacyanoferrate(III); potassium carbonate; osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / water; tert-butyl alcohol; toluene / 0 °C / Inert atmosphere

2.2: 0.5 h / Inert atmosphere

With osmium(VIII) oxide; oxalyl dichloride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/ml400027y

upstream raw materials:

N-(5-allyloxy-pyrazin-2-yl)-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide

5-allyloxy-pyrazine-2-carboxylic acid potassium salt

(R)-2-(3-chloro-4-(methylsulfonyl)phenyl)-3-cyclopentylpropanoic acid

5-allyloxy-pyrazin-2-ylamine