New enantiomerically enriched aromatic azo compounds useful for the preparation of enantiomerically enriched amino alcohol compound and amino acid compound

Simple SummaryContent extracted from patent full text and abstract with AI.

This invention relates to newly developed enantiomerically enriched aromatic azo compounds, which serve as key intermediates for synthesizing enantiomerically enriched amino alcohols and amino acids. The patent also outlines methods for preparing these compounds and converting them into valuable chiral amino derivatives, which are important in fields such as pharmaceuticals and materials science.

Use CasesContent extracted from patent full text and abstract with AI.

• Production of pharmaceuticals where chiral amino alcohols or amino acids are required as active ingredients or intermediates.
• Synthesis of chiral building blocks for drug discovery and medicinal chemistry research.
• Preparation of enantiomerically pure compounds for agrochemicals or specialty chemical industries.
• Development of chiral ligands or catalysts for use in asymmetric synthesis in organic chemistry.
• Manufacture of biochemical research tools and reagents for protein studies or enzyme reactions.

BenefitsContent extracted from patent full text and abstract with AI.

• Provides access to enantiomerically pure amino alcohols and amino acids, which are crucial for high-efficacy and low-side-effect pharmaceuticals.
• Offers a versatile synthetic pathway that improves the efficiency and selectivity of chiral compound production.
• The described methods allow for the isolation of pure enantiomers, which is challenging yet essential for many high-precision applications.
• Supports downstream chemical transformations and expansions into a wide variety of useful chiral compounds.
• Can accelerate pharmaceutical development by providing ready access to key intermediates with defined stereochemistry.

Technical Classifications (CPCs)

Inventors & Applicants

Patent Abstract

Enantiomerically enriched aromatic azo compounds (A) are new. Enantiomerically enriched aromatic azo compounds (A) of formula (C(R1a)(R)(N=N-Ar 1>)-(CH 2) n-OH) (I) or (C(R1a)(R)(N=N-Ar 1>)-(CH 2) n-O-C(=O)-R2a) (II) are new. Ar 1>chiral aromatic substituent, preferably (6-18C)-aryl, (3-18C)-heteroaryl, (1-15C)-alkyl-(6-18C)-aryl, or (1-15C)-alkyl-(3-20C)-heteroaryl; R : organic substituent, preferably (1-20C)-alkyl, (2-20C)-alkenyl, (2-20C)-alkynyl, (2-20C)-alkoxyalkyl, (6-18C)-aryl, (7-40C)-arylalkyl, (3-18C)-heteroaryl, (1-20C)-heteroalkyl, (1-15C)-alkyl-(6-18C)-aryl, (1-15C)-alkyl-(3-20C)-heteroaryl, (3-8C)-cycloalkyl, (1-15C)-alkyl-(3-8C)-cycloalkyl, (3-8C)-cycloalkyl-(1-15C)-alkyl, (1-20C)-alkyl-CO 2H, or (1-20C)-alkyl-CO 2-(1-20C)-alkyl; R1a : (1-20C)-alkyl, preferably CH 3, C 2H 5, n-propyl, isopropyl, n-butyl, (2-20C)-alkenyl, (2-20C)-alkynyl, (2-20C)-alkoxyalkyl, (6-18C)-aryl, (7-40C)-arylalkyl, (3-18C)-heteroaryl, (1-20C)-heteroalkyl, (1-15C)-alkyl-(6-18C)-aryl, (1-15C)-alkyl-(3-20C)-heteroaryl, (3-8C)-cycloalkyl, (1-15C)-alkyl-(3-8C)-cycloalkyl or (3-8C)-cycloalkyl-(1-15C)-alkyl; n : 1-3; and R2a : (1-20C)-alkyl, preferably CH 3, C 2H 5, n-propyl, isopropyl, n-butyl, (2-20C)-alkenyl, (2-20C)-alkynyl, (2-20C)-alkoxyalkyl, (6-18C)-aryl, (7-40C)-arylalkyl, (3-18C)-heteroaryl, (1-20C)-heteroalkyl, (1-15C)-alkyl-(6-18C)-aryl, (1-15C)-alkyl-(3-20C)-heteroaryl, (3-8C)-cycloalkyl, (1-15C)-alkyl-(3-8C)-cycloalkyl, or (3-8C)-cycloalkyl-(1-15C)-alkyl. Independent claims are included for: (1) the preparation of (A); (2) the preparation of an enantiomerically enriched amino alcohol compound of formula (C(R1a)(CH 2-R)(NH 2)-(CH 2) n-OH) (III) comprising (a) conversion of racemate (II) into enantiomerically enriched (A) and (b) reducing (A), where the isolated and pure compounds of (I) or (II) are used; and (3) the preparation of enantiomerically enriched amino acid compound of formula (C(R1a)(CH 2-R)(NH 2)-C(=O)OH) (IV) comprising carrying out the steps (a) and (b), and oxidizing (III).