141109-16-2

Basic information

• Product Name: (R)-(-)-2-CHLOROPHENYLGLYCINE METHYL ESTER
• Synonyms: (R)-(-)-2-CHLOROPHENYLGLYCINE METHYL ESTER;Benzeneacetic acid, a-aMino-2-chloro-, Methyl ester, (aR)-
• CAS NO: 141109-16-2
• Molecular Formula: C₉H₁₀ClNO₂
• Molecular Weight: 199.63
• Product Categories: chiral
• Mol File: 141109-16-2.mol

Chemical Properties

• Boiling Point: 270.097 °C at 760 mmHg
• Flash Point: 117.151 °C
• Appearance: /
• Density: 1.258 g/cm³
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: 1.551
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Sligh
• CAS DataBase Reference: (R)-(-)-2-CHLOROPHENYLGLYCINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-2-CHLOROPHENYLGLYCINE METHYL ESTER(141109-16-2)
• EPA Substance Registry System: (R)-(-)-2-CHLOROPHENYLGLYCINE METHYL ESTER(141109-16-2)

Safety Data

• Hazardous Substances Data: 141109-16-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(R)-(-)-2-Chlorophenylglycine Methyl Ester is used as a starting material for the synthesis of bioactive molecules, which are crucial in the development of new pharmaceuticals. Its role in the creation of secondary metabolites makes it a valuable asset in the search for novel drug candidates and therapeutic agents.
Used in Chemical Research:
In the field of chemical research, (R)-(-)-2-Chlorophenylglycine Methyl Ester is employed as a building block for the synthesis of complex organic compounds. Its unique structure allows for the exploration of new chemical reactions and the development of innovative synthetic pathways, contributing to the advancement of chemical science.
Used in Drug Synthesis:
(R)-(-)-2-Chlorophenylglycine Methyl Ester is used as a key intermediate in the synthesis of various drugs, particularly those targeting specific biological pathways or receptors. Its versatility in chemical reactions enables the creation of a wide range of pharmaceutical compounds with potential therapeutic applications.
Used in Biosynthesis of Secondary Metabolites:
(R)-(-)-2-Chlorophenylglycine Methyl Ester is utilized in the biosynthesis of secondary metabolites, which are organic compounds produced by living organisms that are not essential for their growth or reproduction but can have significant biological activities. These secondary metabolites can be used in the development of new drugs, agrochemicals, or other bioactive compounds with potential applications in various industries.

InChI:InChI=1/C9H10ClNO2/c1-13-9(12)8(11)6-4-2-3-5-7(6)10/h2-5,8H,11H2,1H3/t8-/m1/s1

Upstream product

• 1253091-76-7 methyl 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate 
• 86169-24-6 2-amino-(2-chlorophenyl)ethanoic acid 
• 141109-14-0 2-(2-chlorophenyl)glycine methyl ester hydrochloride 
• 67-56-1 methanol 
• 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 
• 1001414-68-1 (R)-(-)-methyl 2-(tert-butoxycarbonylamino)-2-(2-chlorophenyl)acetate 
• 141109-18-4 (S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride 
• 120202-66-6 (S)-(+)-clopidogrel bisulfate 
• 141109-15-1 2-chlorophenylglycine methyl ester L-(+)-tartaric acid 
• 141109-14-0 methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate 
• 113665-84-2 (S)-(+)-clopidogrel 
• 34966-49-9 methyl 2-chlorobenzoylformate 
• 1396607-35-4 methyl (S)-(+)-2-(2-chlorophenyl)-2-(4,5-dihydrothieno[2,3-c]pyridine-6(7H)-yl)acetate hydrochloride 
• 144750-52-7 methyl 2-(2-chlorophenyl)-2-(4,5-dihydrothieno[2,3-c]pyridine-6(7H)-yl)acetate hydrochloride 
• 1396841-05-6 methyl (S)-(+)-2-(2-chlorophenyl)-2-(4,5-dihydrothieno[2,3-c]pyridin-6(7H)-yl)acetate 
• 144457-43-2 methyl 2-(2-chlorophenyl)-2-(4,5-dihydrothieno[2,3-c]pyridin-6(7H)-yl)acetate 
• 1314028-89-1 methyl (S)-(+)-2-(2-(thiophen-3-yl)ethylamino)-2-(2-chlorophenyl)acetate 
• 1427465-90-4 methyl 2-(2-(thiophen-3-yl)ethylamino)-2-(2-chlorophenyl)acetate 

Relevant articles and documents

Asymmetric Hydrocyanation of N-Phosphinoyl Aldimines with Acetone Cyanohydrin by Cooperative Lewis Acid/Onium Salt/Br?nsted Base Catalysis

α-Amino acids are of fundamental importance for life. Both natural and artificial α-amino acids also play a crucial role for pharmaceutical purposes. The catalytic asymmetric Strecker reaction still provides one of the most attractive strategies to prepare scalemic α-amino acids. Here we disclose a new concept for Strecker reactions, in which an achiral Br?nsted base cooperates with a Lewis acid and an aprotic ammonium salt, which are both arranged in the same chiral catalyst entity. The described method could successfully address various long-standing practical issues of this reaction type. The major practical advantages are that (1) the N-protecting group is readily removable, (2) acetone cyanohydrin is attractive as cyanation reagent in terms of atom economy and cost efficiency, (3) an excess of the cyanation reagent is not necessary, (4) the new method does not require additives and (5) is performed at ambient temperature.

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.

Chemo-enzymatic approach to the synthesis of the antithrombotic clopidogrel

The (S)-2-chlorophenylglycine moiety is well recognized in the structure of (S)-clopidogrel, a known antithrombotic drug. We prepared an enantiomerically pure chiral building block via an enzyme-catalyzed resolution of (RS)-N-Boc-2-chlorophenylglycine methylester. The best results were obtained by means of an immobilized subtilisin, the cross-linked enzyme aggregate (Alcalase-CLEA). The high enantiomeric excess of the synthon obtained remained the same over the course of clopidogrel synthesis; the simplicity of the process makes this pathway suitable for large-scale preparation.

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.