891183-50-9

Usage

Uses

Used in Pharmaceutical Industry:
(S)-4,4-Dimethyl-pyrrolidine-2-carboxylic acid is used as a building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicinal compounds. Its chiral nature allows for the creation of enantiomerically pure substances, which is crucial for ensuring the desired biological activity and minimizing potential side effects.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-4,4-Dimethyl-pyrrolidine-2-carboxylic acid is utilized as a chiral auxiliary, aiding in asymmetric synthesis to produce enantiomerically enriched products. This application is vital for the creation of complex organic molecules with specific stereochemistry, which is essential for biological activity and selectivity.
Used in Chemical Process Development:
(S)-4,4-Dimethyl-pyrrolidine-2-carboxylic acid is employed in the development of new chemical processes, where its unique properties can be leveraged to improve reaction yields, selectivity, and efficiency. This contributes to advancements in chemical manufacturing and the production of high-quality chemical products.
Used in Material Science:
(S)-4,4-Dimethyl-pyrrolidine-2-carboxylic acid also has potential applications in material science, where it can be incorporated into the design and synthesis of new materials with tailored properties. This may include the development of novel polymers, catalysts, or other advanced materials that can be used across various industries.

Upstream product

• 63624-44-2 3-chloro-5,5-dimethyl-piperidin-2-one 
• 156088-46-9 (5S)-3,3-dimethyl-5-hydroxymethylpyrrolidin-2-one 
• 156088-45-8 (5S)-1-aza-2,2-dimethyl-7,7-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane 
• 1001353-86-1 (S)-4,4-dimethylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 57224-50-7 (S)-2-Amino-4,4-dimethyl-pentanoic acid 
• 212890-85-2 (S)-(+)-(4,4-dimethylpyrrolidin-2-yl)methan-1-ol 
• 99208-71-6 (5S)-1-aza-2,2-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane 
• 443984-28-9 (S)-(N-benzyloxycarbonyl)-(4,4-dimethylpyrrolidin-2-yl)methan-1-ol 
• 1001353-87-2 (2S)-1-(tert-butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

Remote C-H Hydroxylation by an α-Ketoglutarate-Dependent Dioxygenase Enables Efficient Chemoenzymatic Synthesis of Manzacidin C and Proline Analogs

Selective C-H functionalization at distal positions remains a highly challenging problem in organic synthesis. Though Nature has evolved a myriad of enzymes capable of such feat, their synthetic utility has largely been overlooked. Here, we functionally characterize an α-ketoglutarate-dependent dioxygenase (Fe/αKG) that selectively hydroxylates the ? position of various aliphatic amino acids. Kinetic analysis and substrate profiling of the enzyme show superior catalytic efficiency and substrate promiscuity relative to other Fe/αKGs that catalyze similar reactions. We demonstrate the practical utility of this transformation in the concise syntheses of a rare alkaloid, manzacidin C, and densely substituted amino acid derivatives with remarkable step efficiency. This work provides a blueprint for future applications of Fe/αKG hydroxylation in complex molecule synthesis and the development of powerful synthetic paradigms centered on enzymatic C-H functionalization logic.

Evolution of Biocatalytic and Chemocatalytic C-H Functionalization Strategy in the Synthesis of Manzacidin C

Because of their unique molecular architecture, the manzacidins have been the subject of intense synthetic efforts in the past two decades. Here, we describe two synthetic approaches toward manzacidin C that center on the enzymatic hydroxylation of unprotected l-leucine. This study also resulted in the discovery of novel synthetic methodologies, including a photocatalytic C-H azidation of unprotected amino acids. Additionally, we describe the use of hydroxylated l-leucine in the preparation of various densely substituted pyrrolidines.

PYRROLOTRIAZINE KINASE INHIBITORS

The invention provides compounds of formula I and pharmaceutically acceptable salts thereof. The formula I compounds inhibit tyrosine kinase activity thereby making them useful as anticancer agents and for the treatment of Alzheimer's Disease.

4,4′-Disubstituted L-prolines as highly enantioselective catalysts for direct aldol reactions

A new series of 4,4′-disubstituted prolines (1a-h) has been developed and tested as organocatalysts in the direct catalytic asymmetric aldol reaction of several aliphatic ketones with aldehydes. Catalyst 1g affords the best enantioselectivities for this transformation. The reaction was carried out in DMF using a catalyst loading of 10 mol% at -10°C to give the aldol products in up to 97% ee for acetone. In the cases of cyclohexanone and cyclopentanone, the corresponding anti-products were obtained in 94% ee.

Bicyclic 6-alkylidene-penems as class-D beta-lactamases inhibitors

This invention relates to certain bicyclic 6-alkylidene penems which act as a inhibitor of class-D enzymes. β-Lactamases hydrolyze β-lactam antibiotics, and as such serve as the primary cause of bacterial resistance. The compounds of the present invention when combined with β-lactam antibiotics will provide an effective treatment against life threatening bacterial infections. In accordance with the present invention there are provided compounds of general formula I or a pharmaceutically acceptable salt or in vivo hydrolyzable ester R5 thereof: wherein: One of A and B denotes hydrogen and the other an optionally substituted fused bicyclic heteroaryl group; and X═O or S.

Process for preparing 6-alkylidene penem derivatives

The present invention provides a process of making compounds of formula I, which are useful for the treatment of bacterial infection or disease.

BICYCLIC 6-ALKYLIDENE-PENEMS AS ?-LACTAMASES INHIBITORS

The present invention provides a compound of Formula (I), pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.