210883-78-6

Usage

Uses

Used in Medicinal Chemistry:
(R)-1-((R)-1-Phenylethyl)azetidine-2-carboxylic acid is used as a building block for the synthesis of various pharmaceutical compounds due to its unique azetidine ring and carboxylic acid functional group. Its chiral nature allows for the development of enantiomerically pure drugs, which can have significant implications in terms of efficacy and safety.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-1-((R)-1-Phenylethyl)azetidine-2-carboxylic acid is used as an intermediate in the development of new drugs. Its structural features may contribute to the discovery of novel therapeutic agents with improved pharmacological profiles.
Used in Research and Development:
(R)-1-((R)-1-Phenylethyl)azetidine-2-carboxylic acid serves as a valuable compound in research and development for understanding the relationship between chemical structure and biological activity. It can be used to study the effects of stereochemistry on drug action and to develop new methodologies for the synthesis of chiral pharmaceuticals.

Upstream product

• 921600-20-6 dimethyl (1'S)-1-(1'-methyl)benzylazetidine-2,2-dicarboxylate 
• 204274-29-3 methyl (2S,1'S)-1-(1'-methyl)benzylazetidine-2-carboxylate 
• 921600-22-8 dimethyl (1'S)-(1'-methyl)benzylaminomalonate 
• 204274-30-6 methyl (2R,1'S)-1-(1'-methyl)benzylazetidine-2-carboxylate 

Relevant academic research and scientific papers

Efficient route to (S)-azetidine-2-carboxylic acid

A new and efficient route to (S)-azetidine-2-carboxylic acid (>99.9% ee) in five steps and total yield of 48% via malonic ester intermediates was established. As the key step, efficient four-membered ring formation (99%) was achieved from dimethyl (S)-(1′-methyl)benzylaminomalonate by treating with 1,2-dibromoethane (1.5 eq) and cesium carbonate (2 eq) in DMF. Krapcho dealkoxycarbonylation of dimethyl (1′S)-1-(1′-methyl) benzylazetidine-2,2-dicarboxylate, the product of this cyclization procedure, proceeded with preferential formation (2.7:1, 78% total yield) of the desired (2S,1′S)-monoester, with the help of a chiral auxiliary which was introduced on the nitrogen atom. The undesired (2R,1′S)-isomer could be converted to that with proper stereochemistry, by a deprotonation and subsequent reprotonation step. Finally, lipase-catalyzed preferential hydrolysis of the (2S,1′S)-monoester and subsequent deprotection provided enantiomerically pure (S)-azetidine-2-carboxylic acid in a 91% yield from the mixture of (2S,1′S)- and (2R,1′S)-isomers.

Process for producing optically active azetidine-2-carboxylic acid derivative

There is provided a process for improving optical purity of azetidine-2-carboxylic acid of the following formula which comprises: preparing a solution of azetidine-2-carboxylic acid; and cooling the said solution in the presence of a seed crystal of one optional optical isomer of the azetidine-2-carboxylic acid to selectively recrystallize the optical isomer of the azetidine-2-carboxylic acid having the same configuration with respect to the carbon atom of the 2-position of the azetidine ring as the seed crystal.