3972-40-5

Usage

Uses

Used in Organic Synthesis:
(R)-2-CHLOROSUCCINIC ACID is used as a building block in organic synthesis for the creation of pharmaceuticals and other organic compounds. Its unique chiral properties allow for the development of enantioselective reactions, leading to the production of specific enantiomers with desired biological activities.
Used in Pharmaceutical Industry:
(R)-2-CHLOROSUCCINIC ACID is used as a key intermediate in the synthesis of chiral drugs, contributing to the development of more effective and safer medications. Its ability to induce enantioselectivity in chemical reactions is crucial for producing single enantiomers with targeted therapeutic effects.
Used in Chiral Resolving Agent:
(R)-2-CHLOROSUCCINIC ACID serves as a chiral resolving agent for the separation of racemic mixtures. This application is vital in obtaining pure enantiomers, which can exhibit different biological activities and reduce potential side effects associated with racemic compounds.
Used in Asymmetric Catalysis:
(R)-2-CHLOROSUCCINIC ACID has potential applications in the field of asymmetric catalysis, where it can be employed as a catalyst or ligand to induce enantioselectivity in chemical reactions. This contributes to the production of chiral, biologically active compounds with improved selectivity and efficiency.

InChI:InChI=1/C4H5ClO4/c5-2(4(8)9)1-3(6)7/h2H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1

Upstream product

• 97-67-6 (S)-Malic acid 
• 923-06-8 bromosuccinic acid 
• 617-45-8 aspartic Acid 
• 56-84-8 L-Aspartic acid 
• 1783-96-6 (2R)-aspartic acid 
• 28374-86-9 3-chlorohexa-1,5-diene 
• 7647-01-0 hydrogenchloride 
• 4198-33-8 (2S)-chlorobutanedioic acid 

Downstream Products

• 111618-88-3 dimethyl (2R)-chlorobutanedioate 

Relevant academic research and scientific papers

Asymmetric Synthesis of Atorvastatin Calcium through Intramolecular Oxidative Oxygen-Nucleophilic Bromocyclization

The stereocontrolled synthesis of atorvastatin calcium starting from commercially available d-aspartic acid using an intramolecular oxidative oxygen-nucleophilic bromocyclization of a homoallylic tert-butyl carbonate is described. This strategy allows the formation of the chiral syn-1,3-diol moiety with the desired stereochemistry, and provides a functionalized bromomethyl group for the construction of the atorvastatin side-chain with high regio- and diastereoselectivity. This route is attractive as it represents an efficient and environmentally sensitive approach to the large-scale synthesis of statins and their analogues.

Identification and pharmacological characterization of succinate receptor agonists

Background and Purpose: The succinate receptor (formerly GPR91 or SUCNR1) is described as a metabolic sensor that may be involved in homeostasis. Notwithstanding its implication in important (patho)physiological processes, the function of succinate receptors has remained ill-defined because no pharmacological tools were available. We report on the discovery of the first family of potent synthetic agonists. Experimental Approach: We screened a library of succinate analogues and analysed their activity on succinate receptors. Also, we modelled a pharmacophore and a binding site for this receptor. New agonists were identified based on the information provided by these two approaches. Their activity was studied in various bioassays, including measurement of cAMP levels, [Ca2+]i mobilization, TGF-α shedding and recruitment of arrestin 3. The in vivo effects of activating succinate receptors with these new agonists was evaluated on rat BP. Key Results: We identified cis-epoxysuccinic acid and cis-1,2-cyclopropanedicarboxylic acid as agonists with an efficacy similar to that of succinic acid. Interestingly, cis-epoxysuccinic acid was 10- to 20-fold more potent than succinic acid on succinate receptors. For example, cis-epoxysuccinic acid reduced cAMP levels with a pEC50?=?5.57?±?0.02 (EC50?=?2.7?μM), compared with succinate pEC50?=?4.54?±?0.08 (EC50?=?29?μM). The rank order of potency of the three agonists was the same in all in vitro assays. Both cis-epoxysuccinic and cis-1,2-cyclopropanedicarboxylic acid were as potent as succinate in increasing rat BP. Conclusions and Implications: We describe new agonists at succinate receptors that should facilitate further research on this understudied receptor.

Accessing Centnerszwer's quasiracemate-molecular shape controlled molecular recognition

M. Centnerszwer's seminal 1899 report investigated the stereochemical relationship between optical antipodes of different substances using melting-point behavior. One intriguing melting-point phase diagram produced from this early investigation combined (+)-2-chlorosuccinic acid [(+)-1] and (-)-2-bromosuccinic acid [(-)-2]. While Centnerszwer's data clearly indicates the formation of a quasiracemic phase-i.e., materials constructed from pairs of isosteric molecules of opposite handedness-at the 1:1 component ratio, this material is energetically less favorable than the chiral counterparts. The consequence of this crystal instability is significant as evident by the absence of literature sited crystal structures for the quasiracemic phase (+)-1/(-)-2 and racemates (±)-1 and (±)-2. This study circumvented this challenge by generating multi-molecular assemblies using additional crystallizing agents capable of complementing the hydrogen-bond abilities of succinic acids 1 and 2. Both imidazole (Im) and 4,4′-bipyridyl-N,N′-dioxide (BPDO) served as tailor-made additives that effectively modified the crystal packing landscape of quasiracemate of (+)-1/(-)-2. Combining imidazole with the quasiracemate, racemate, and enantiopure forms of 1 and 2 resulted in crystal structures characterized as molecular salts with layered motifs formed from highly directional N+-H?carboxylate and carboxyl?carboxylate interactions. In contrast to the enantiopure [(+)-1·Im and (-)-2·Im] and racemic [(±)-1·Im and (±)-2·Im] systems, neighboring molecular layers observed in quasiracemate (+)-1/(-)-2·Im are organized by approximate inversion symmetry. Assessment of the crystal packing efficiency for this series of molecular salts via crystal densities and packing coefficients (Ck) indicates imidazole greatly alters the crystal landscape of the system in favor of racemic and quasiracemic crystal packing. A similar desymmetrized crystal environment was also realized for the ternary cocrystalline system of (+)-1/(-)-2·BPDO where the components organize via N+-O-?carboxyl contacts. This study underscores the importance of molecular shape to molecular recognition processes and the stabilizing effect of tailor-made additives for creating new crystalline phases of previously inaccessible crystalline materials.

Application of (2)H N.M.R. Spectroscopy to Study the Incorporation of Enantiomeric -Labelled Putrescines into the Pyrrolizidine Alkaloid Retrorsine

A sample of (2R)-putrescine (13) dihydrochloride was prepared from (2S)-aspartic acid (8), and (2S)-putrescine (15) dihydrochloride was synthesized from (2R)-aspartic acid.Feeding experiments carried out with these precursors on Senecio isatideus plants gave retrorsine (5) containing (2)H, and the distribution of (2)H from each experiment in retrorsine was determined by (2)H n.m.r. spectroscopy.All of the (2)H was confined to the base component of the alkaloid, retronecine (4).Retrorsine (14), derived biosynthetically from (2R)-putrescine (13) dihydrochloride was labelled with (2)H at C-2 and C-6α, while retrorsine (16), produced from (2S)-putrescine (15) dihydrochloride contained (2)H labels at C-6β and C-7α.These labelling patterns demonstrate that hydroxylation at C-7 of retronecine (4) proceeds with retention of configuration.In addition, the formation of the 1,2-double bond of retronecine involves removal of the pro-S hydrogen and retention of the pro-R hydrogen at the carbon atom which becomes C-2 of retronecine.