Desbenzyl N-Acetyl-di-O-acetyl KRP-203

Base Information

• Chemical Name: Desbenzyl N-Acetyl-di-O-acetyl KRP-203
• CAS No.: 951238-24-7
• Molecular Formula: C23H26ClNO6S
• Molecular Weight: 479.982
• DSSTox Substance ID: DTXSID70587838
• Wikidata: Q82480328
• Mol file: 951238-24-7.mol

Synonyms:Desbenzyl N-Acetyl-di-O-acetyl KRP-203;951238-24-7;[2-acetamido-2-(acetyloxymethyl)-4-[2-chloro-4-(3-hydroxyphenyl)sulfanylphenyl]butyl] acetate;SCHEMBL590688;DTXSID70587838;2-Acetamido-2-[(acetyloxy)methyl]-4-{2-chloro-4-[(3-hydroxyphenyl)sulfanyl]phenyl}butyl acetate

Chemical Property of Desbenzyl N-Acetyl-di-O-acetyl KRP-203

Chemical Property:

• Melting Point: 142-143 °C
• Boiling Point: 683.0±55.0 °C(Predicted)
• PKA: 9.29±0.10(Predicted)
• PSA: 130.72000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 4.97080
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 479.1169364
• Heavy Atom Count: 32
• Complexity: 630

Purity/Quality:

98% ^*data from raw suppliers

DesbenzylN-Acetyl-di-O-acetylKRP-203 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CCC1=C(C=C(C=C1)SC2=CC=CC(=C2)O)Cl)(COC(=O)C)COC(=O)C
• Uses: As KRP-203 derivative, Desbenzyl N-Acetyl-di-O-acetyl can be used as intermediate in the preparation of 2-aminobutanol derivatives used in the treatment of autoimmune diseases.

Technology Process of Desbenzyl N-Acetyl-di-O-acetyl KRP-203

There total 1 articles about Desbenzyl N-Acetyl-di-O-acetyl KRP-203 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: 86.0%

2-acetamido-2-[2-(4-bromo-2-chlorophenyl)ethyl]propane-1,3-diol diacetate (951238-23-6) + 3-mercaptophenol (40248-84-8) → N-{1,1-bis(acetoxymethyl)-3-[2-chloro-4-(hydoxyphenylthio)phenyl]propyl}acetamide (951238-24-7)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; at 120 ℃; for 9h;

DOI:10.1055/s-2007-983721

Reference yield: 97.0%

N-{1,1-bis(acetoxymethyl)-3-[2-chloro-4-(hydoxyphenylthio)phenyl]propyl}acetamide (951238-24-7) + benzyl bromide (100-39-0) → N-{3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]-1,1-bis(acethoxymethyl)propyl}acetamide (951238-25-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1055/s-2007-983721

Reference yield:

N-{1,1-bis(acetoxymethyl)-3-[2-chloro-4-(hydoxyphenylthio)phenyl]propyl}acetamide (951238-24-7) + benzyl bromide (100-39-0) → KRP203

Guidance literature:

N-{1,1-bis(acetoxymethyl)-3-[2-chloro-4-(hydoxyphenylthio)phenyl]propyl}acetamide; benzyl bromide; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

With lithium hydroxide; water; In tetrahydrofuran; methanol; at 80 ℃; for 2h;

With hydrogenchloride; In 1,4-dioxane; dichloromethane;

upstream raw materials:

2-acetamido-2-[2-(4-bromo-2-chlorophenyl)ethyl]propane-1,3-diol diacetate

3-mercaptophenol

Downstream raw materials:

N-{3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]-1,1-bis(acethoxymethyl)propyl}acetamide

2-amino-2-[2-(4-{[3-(benzyloxy)phenyl]sulfanyl}-2-chlorophenyl)ethyl]propane-1,3-diol

Refernces

• 1、 Hamada, Maiko,Kiuchi, Masatoshi,Adachi, Kunitomo. "Efficient synthesis of the immunomodulating compound KRP-203". . p. 1927 - 1929. Retrieved 2008/02/10.