141109-13-9

Usage

Uses

Used in Pharmaceutical Development:
DL-Chlorophenylglycine methyl ester hydrochloride is utilized as a therapeutic agent for the treatment of neurological disorders. Its application is primarily due to its ability to modulate the overactivity of NMDA receptors, which is implicated in conditions such as epilepsy, neurodegenerative diseases, and ischemic brain injury. By inhibiting excessive glutamate signaling, CGP 37849 may help in reducing the severity and frequency of seizures and protecting neurons from damage.
Used in Neurological Research:
In the field of neuroscience, DL-Chlorophenylglycine methyl ester hydrochloride serves as a valuable research tool. It is used to investigate the role of NMDA receptors in various neurological disorders. DL-Chlorophenylglycine methyl ester hydrochloride aids researchers in understanding the intricate mechanisms of neuronal signaling and synaptic plasticity, which are fundamental to learning, memory, and other cognitive functions. Additionally, it helps in identifying potential therapeutic targets for the development of new drugs to treat neurological conditions.
Used in Drug Discovery and Development:
DL-Chlorophenylglycine methyl ester hydrochloride is employed in drug discovery and development processes as a lead compound. Its antagonistic properties towards NMDA receptors make it a candidate for further optimization and modification to enhance its therapeutic potential. Researchers use CGP 37849 to design and synthesize new molecules with improved pharmacological profiles, aiming to achieve better efficacy, selectivity, and safety in the treatment of neurological disorders.

Upstream product

• 67-56-1 methanol 
• 86169-24-6 2-amino-(2-chlorophenyl)ethanoic acid 
• 1233361-76-6 L-(+)-tartaric acid salt of α-amino-(2-chlorophenyl)acetic acid methyl ester 

Downstream Products

• 92233-02-8 (Ethoxycarbonyl)-4 (o-chlorophenyl)-2 methyl-3 aza-3 butanoate de methyle 
• 141109-15-1 2-chlorophenylglycine methyl ester L-(+)-tartaric acid 
• 141109-16-2 α-amino-(2-chlorophenyl)acetic acid methyl ester 
• 141109-14-0 methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate 
• 113665-84-2 (S)-(+)-clopidogrel 
• 141109-18-4 (S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride 
• 120202-66-6 (S)-(+)-clopidogrel bisulfate 
• 1423136-84-8 methyl 4-benzoyl-2-(2-chlorophenyl)-5-(4-nitrophenyl)-2,5-dihydro-1H-pyrrole-2-carboxylate 
• 1423136-85-9 methyl 4-benzoyl-2-(2-chlorophenyl)-5-(4-nitrophenyl)-2,5-dihydro-1H-pyrrole-2-carboxylate 
• 138228-59-8 (R)-2-(benzylideneamino)-2-(2-chlorophenyl)acetamide 
• 1198213-96-5 2-(benzylideneamino)-2-(2-chlorophenyl)acetamide 
• 1322877-80-4 trimethyl (2S,3S,4R,5S)-2-(2-chlorophenyl)-5-(4-nitrophenyl)pyrrolidine-2,3,4-tricarboxylate 
• 1276118-85-4 C₂₁H₂₃ClN₂O₃ 
• 1276118-84-3 C₂₀H₂₁ClN₂O₃ 

Relevant academic research and scientific papers

Preparation method of clopidogrel hydrogen sulfate intermediate

The present invention relates to a preparation method of a clopidogrel hydrogen sulfate intermediate. (+)-2-chlorophenylglycine methyl ester and alpha-thiopheneethanol p-toluenesulfonate are adopted as raw materials, a reaction solvent and an acid-binding agent are added for a condensation reaction, the condensation reaction process is divided into a first stage and a second stage, and when 60-95% of the condensation reaction is completed, first-stage reaction is completed; after the first-stage reaction is completed, firstly part of the reaction solvent is removed, and then second-stage reaction is carried out; and after the second-stage reaction is completed, a target product is obtained, namely the clopidogrel hydrogen sulfate intermediate. After the first-stage reaction is completed, part of the reaction solvent is removed firstly, and then the second-stage reaction is continued, so that the concentration of the reaction material can be increased in the later stage of the condensation reaction, the use amount of the reaction solvent is reduced, and racemization and side reaction in the reaction process are effectively inhibited, thereby improving the chiral purity of the product, increasing the yield, reducing the use of auxiliary materials greatly, and reducing the production cost.

Preparation method of sulfonic clopidogrel impurity

The invention discloses a preparation method of a sulfonic clopidogrel impurity. The preparation method comprises the following steps: reacting thiophene-2-ethanol with toluenesulfonyl chloride to generate p-toluenesulfonic acid-2-thienylethyl ester; carrying out esterification on o-chlorophenylglycine and methanol to generate o-chlorophenylglycine methyl ester; resolving the o-chlorophenylglycinemethyl ester by using L(+) tartaric acid; converting into free S-(+)-o-chlorophenylglycine methyl ester in dichloromethane; carrying out a condensation reaction on the p-toluenesulfonic acid-2-thienylethyl ester and the S-(+)-o-chlorophenylglycine methyl ester under an alkaline condition; acidifying the obtained product to generate (S)-2-(2-thienylethylamino)(2-chlorphenyl)methyl acetate, carrying out a condensation reaction on the (S)-2-(2-thienylethylamino)(2-chlorphenyl)methyl acetate and formaldehyde to obtain clopidogrel, and carrying out a reaction on the clopidogrel and chlorosulfonicacid to generate sulfonic clopidogrel impurity. The preparation method of the sulfonic clopidogrel impurity has the advantages of mild reaction conditions, accessible raw materials, low cost and highyield and purity.

Synthesis process of anti-cancer drug (glycinate methyl ester)

The invention provides a synthesis process of an anti-cancer drug (glycinate methyl ester). The process includes the steps of firstly, adding methyl alcohol into a flask with a stirrer, a thermometer and a constant-pressure dropping funnel, controlling the temperature at 0-5 DEG C, and slowly dropwise adding acetyl chloride into the flask for thermal insulation reaction for 1.5 hours; secondly, adding o-chlorophenylglycine to be heated to 45 DEG C for reaction for 15 hours; thirdly, conducting depressurized rotary evaporating to remove most of solvent, and conducting separation and suction-filtration to obtain a product (hydrochloride solid); fourthly, dissolving the obtained solid in water, adding dichloromethane, adjusting the pH value to be 7.5 through ammonium hydroxide, extracting a water layer through dichloromethane, combining an organic layer, conducting washing through saturated table salt until the neutral state is reached, conducting drying and suction filtration on anhydrous magnesium sulfate, and conducting depressurized rotary evaporating to remove a solvent to obtain a colorless transparent oily substance. Through the improvement, the synthesis method has the advantages that the process is green and free of pollution, the reaction conditions are mild, the operation is simple, the product can be easily extracted, and the yield is high; thus, the problems and defects in the background are effectively solved and overcome.

A compound clopidogrel hydrogensulfate method for the preparation of

The invention relates to a preparation method of clopidogrel disulfate. The preparation method comprises the following steps of step one. carrying out esterification reaction, namely preparing (+/-) DL-2-Chlorophenylglycine methyl ester; step two. carrying out splitting reaction, namely preparing (+) DL-2-Chlorophenylglycine methyl ester; step three. carrying out activating reaction, namely preparing alpha-thiophene ethanol p-toluenesulfonates; step four. carrying out substitution reaction, namely preparing (+) alpha-(2-thiophene ethylamino)-2-(2-chlorobenzene) methyl acetate hydrochloride; step five. carrying out ring closing reaction, namely preparing clopidogrel; and step six. carrying out salt-forming reaction, namely preparing the clopidogrel disulfate. The preparation method has the advantages that the preparation technology is optimized and improved, reaction conditions are mild, the splitting and the racemization are truly and synchronously carried out, and an obtained crude product has high specific rotation; a catalyst is used in the substitution reaction, so that the reaction time is shortened; the ring closing reaction is carried out at 40 DEG C under the condition of avoiding light, so that the purity of the product is relatively high; and the period of the whole synthetic route is shortened, the aftertreatment operation is simple, and therefore, the preparation method is suitable for mass production.

Pasteur's Tweezers revisited: On the mechanism of attrition-enhanced deracemization and resolution of chiral conglomerate solids

Insights into the mechanism of attrition-enhanced deracemization and resolution of solid enantiomorphic chiral compounds are obtained by crystal size and solubility measurements and by isotopic labeling experiments. Together these results help to deconvolute the various chemical and physical rate processes contributing to the phenomenon. Crystal size measurements highlight a distinct correlation between the stochastic, transient growth of crystals and the emergence of a single solid enantiomorph under attrition conditions. The rapid mass transfer of molecules between the solution and solid phases under attrition is demonstrated, and the concept of a crystal-size-induced solubility driving force is exploited to overcome the stochastic nature of the crystal growth and dissolution processes. Extension to non-racemizing conditions provides a novel methodology for chiral resolution. Implications both for practical chiral separations and for the origin of biological homochirality are discussed.

Novel analogues of ketamine and phencyclidine as NMDA receptor antagonists

The identification of structurally novel analogues of ketamine and phencyclidine (PCP), as NMDA receptor antagonists, with low to moderate potency at GluN2A and GluN2B receptors is discussed. In particular, some examples, such as compounds 6 and 10, shows decreased calculated lipophilicity, when compared to PCP, while retaining moderate activity. Moreover, the germinal aryl amino substituted lactam ring, as exemplified in compounds 7-10 and 11-13, constitutes a novel scaffold with potential application in the design of biologically active compounds.

Attrition-enhanced deracemization in the synthesis of clopidogrel - A practical application of a new discovery

The recently discovered technique of deracemization by means of attrition-induced grinding of a solid conglomerate in contact with a solution wherein racemization occurs has been used with a derivative of 2-chlorophenyl glycine, the key chiral component in the synthesis of Clopidogrel (Plavix). Deracemization of the racemate proceeds to a single enantiomer and in essentially absolute enantiomeric excess. Further conversion of enantiomerically pure material to Clopidogrel was achieved in 88% yield.

PROCESS FOR PREPARING CLOPIDOGREL

A process for preparing clopidogrel or a salt thereof.

PROCESS FOR PREPARATION OF CLOPIDOGREL BISULPHATE FORM-1

Disclosed herein is a cost effective and industrially feasible process for the preparation of (+) Clopidogrel bisulphate. The present invention further discloses a novel method of precipitation of (+) Clopidogrel bisulphate Form I directly from solvent mix of methanol and acetone in presence of sulfuric acid at a temperature of 25-40° C.

Racemization of optically active 2-substituted phenyl glycine esters

A process for preparing racemic mixtures containing nearly equal amounts of stereo isomers of compounds of formula (I), or their salts, by heating an enantiomerically enriched material with thionyl chloride. A required useful enantiomer may thereby be recovered from unwanted mother liquors that would otherwise be otherwise be discarded.