951238-24-7

Usage

Uses

Used in Pharmaceutical Industry:
Desbenzyl N-Acetyl-di-O-acetyl KRP-203 is used as an intermediate in the synthesis of 2-aminobutanol derivatives for the treatment of autoimmune diseases. Its role in the preparation process is crucial for developing effective medications to manage these conditions.

Upstream product

• 951238-23-6 2-acetamido-2-[2-(4-bromo-2-chlorophenyl)ethyl]propane-1,3-diol diacetate 
• 40248-84-8 3-mercaptophenol 

Downstream Products

• 951238-25-8 N-{3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]-1,1-bis(acethoxymethyl)propyl}acetamide 
• 509092-16-4 2-amino-2-[2-(4-{[3-(benzyloxy)phenyl]sulfanyl}-2-chlorophenyl)ethyl]propane-1,3-diol 

Relevant academic research and scientific papers

2-AMINOBUTANOL COMPOUND AND USE THEREOF FOR MEDICAL PURPOSES

The present invention provides a novel compound having few side effects such as bradycardia and the like and having superior peripheral blood lymphocyte-decreasing effect. The present invention provides a 2-aminobutanol compound represented by the following formula (I) wherein R1 is a hydrogen atom or P(=O)(OH)2, R2 is an alkyl having 1 to 4 carbon atoms optionally substituted by hydroxyl group(s) or optionally substituted by halogen atom(s), R3 is a hydrogen atom; a halogen atom; cyano; an alkyl having 1 to 4 carbon atoms optionally substituted by halogen atom(s); or an acyl having 2 to 5 carbon atoms optionally substituted by halogen atom(s), X is an oxygen atom, a sulfur atom, carbonyl or NR4 wherein R4 is a hydrogen atom or an alkyl having 1 to 4 carbon atoms, Ar1 is an optionally substituted arylene or an optionally substituted heteroarylene, and Ar2 is an optionally substituted aryl or an optionally substituted heteroaryl, provided that when X is an oxygen atom, Ar1 is phenylene and Ar2 is phenyl, then the phenyl for Ar2 should be substituted, or a pharmaceutically acceptable acid addition salt thereof, or a hydrate thereof, or a solvate thereof, as well as a production method of the above-mentioned 2-aminobutanol compound.

Efficient synthesis of the immunomodulating compound KRP-203

A practical and concise synthesis of KRP-203 (1) was achieved by utilizing a palladium coupling reaction mediated by XantPhos and Pd2(dba) 3 as the key step. The coupling reaction of aryl bromide 5 with 3-hydroxythiophenol (6) proceeded chemoselectively to give phenol 7 in spite of the presence of a chlorine substituent on 5 and a hydroxyl group on 6. Phenol 7 was converted into KRP-203 by benzylation and removal of the protecting groups in high yield. Georg Thieme Verlag Stuttgart.