42258-90-2

Basic information

• Product Name: methyl (R)-thiazolidine-4-carboxylate
• Synonyms: methyl (R)-thiazolidine-4-carboxylate;4-Thiazolidinecarboxylicacid,methylester,(4R)-(9CI);(4R)-Thiazolidine-4-carboxylic acid methyl ester;(R)-4α-Thiazolidinecarboxylic acid methyl ester;(R)-Thiazolidine-4α-carboxylic acid methyl ester;(R)-methyl thiazolidine-4-carboxylate;methyl (4R)-1,3-thiazolidine-4-carboxylate
• CAS NO: 42258-90-2
• Molecular Formula: C₅H₉NO₂S
• Molecular Weight: 147.19546
• EINECS: 255-739-3
• Product Categories: CARBOXYLICESTER
• Mol File: 42258-90-2.mol

Chemical Properties

• Boiling Point: 238.9 °C at 760 mmHg
• Flash Point: 98.3 °C
• Appearance: /
• Density: 1.208 g/cm³
• Vapor Pressure: 0.0413mmHg at 25°C
• Refractive Index: 1.507
• CAS DataBase Reference: methyl (R)-thiazolidine-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (R)-thiazolidine-4-carboxylate(42258-90-2)
• EPA Substance Registry System: methyl (R)-thiazolidine-4-carboxylate(42258-90-2)

Safety Data

• Hazardous Substances Data: 42258-90-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl (R)-thiazolidine-4-carboxylate is utilized as a key building block in the synthesis of pharmaceuticals, owing to its unique structure and properties that facilitate the creation of new drug candidates.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, methyl (R)-thiazolidine-4-carboxylate is employed as a valuable tool for drug discovery, particularly in the development of drugs targeting diabetes and obesity, due to its potential pharmacological activity and the specific spatial arrangement of its atoms indicated by its (R) configuration.
Used in Organic Compound Synthesis:
Methyl (R)-thiazolidine-4-carboxylate is also used in the synthesis of other organic compounds, leveraging its structural features to contribute to the development of novel chemical entities with potential applications in various industries.

InChI:InChI=1/C5H9NO2S/c1-8-5(7)4-2-9-3-6-4/h4,6H,2-3H2,1H3/t4-/m0/s1

Upstream product

• 34592-47-7 L-thioproline 
• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 52-89-1 l-cysteine hydrochloride 
• 2485-62-3 L-Cysteine methyl ester 
• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 67089-84-3 (R)-thiazolidine-4-carboxylic acid hydrochloride 
• 110-88-3 1,3,5-Trioxan 
• 5714-80-7 D-cysteine methyl ester hydrochloride 

Downstream Products

• 86634-64-2 (R)-6-phenyl-5-thioxotetrahydroimidazo[1,5-c]thiazol-7(3H)-one 
• 479586-30-6 (R)-3-[(R)-3-tert-Butoxycarbonylamino-4-(2-fluoro-phenyl)-butyryl]-thiazolidine-4-carboxylic acid methyl ester 
• 156320-26-2 (R)-Thiazolidine-4-carboxylic acid hydrazide 
• 59418-09-6 4-thiazolecarboxylate methyl ester 
• 105126-41-8 chloro-3 nitro-5 indazole 
• 105126-40-7 (R)-6-Cyclohexyl-dihydro-imidazo[1,5-c]thiazole-5,7-dione 
• 105126-43-0 (R)-6-(4-Methoxy-phenyl)-dihydro-imidazo[1,5-c]thiazole-5,7-dione 
• 105126-42-9 (R)-6-p-Tolyl-dihydro-imidazo[1,5-c]thiazole-5,7-dione 
• 51977-23-2 6,8-dioxo-7-phenyl-3-thia-1,7-diazabicyclo<3.3.0>octane 
• 105126-44-1 (R)-6-(4-Chloro-phenyl)-dihydro-imidazo[1,5-c]thiazole-5,7-dione 

Relevant articles and documents

Stereochemical study of 1,3-N,X-heterocycles derived from α-aminoacids and formaldehyde. Structural evidence for the existence of the anomeric effect

We have shown that condensation of L-cysteine methyl ester (8) and L-threonine methyl ester (11) with formaldehyde provides a convenient and efficient access to novel heterocyclic 2:3 adducts. Depending on the amino acid, the condensation leads to either the N,N′-methylenebis(thiazolidine) (10, L-cys) or -(oxazolidine) (13, L-thr) derivative or to its bicyclo[4.4.1]undecane isomer (5, L-ser) as the major product of the reaction. The structure of 10, 12 and 13, was unambiguously confirmed by diffraction analysis and/or NMR spectroscopy. The latter proved to be a powerful tool to discriminate between the two possible isomers. X-Ray data emphasized the contribution of stereoelectronic effects to the structure of the above compounds.

Method for preparing thiazole-4-formic acid

The invention discloses a method for preparing thiazole-4-formic acid. By the aid of the method, the problems of relatively high prices of raw materials used in old processes for thiabendazole which is one of important traditional pesticide and bactericide varieties and low yield of the thiabendazole can be solved. The method includes steps of generating thiazolidine-4-formic acid from L-cysteinehydrochloride, formaldehyde and pyridine; carrying out reaction on the thiazolidine-4-formic acid, methyl alcohol and HCl gas to generate thiazolidine-4-methyl formate; carrying out reaction on the thiazolidine-4-methyl formate, acetonitrile and MnO2 to generate thiazole-4-methyl formate; hydrolyzing the thiazole-4-methyl formate under the effect of sodium hydroxide to obtain the thiazole-4-formicacid which is a product. The method has the advantages of simple process synthetic route, mild reaction condition, low cost, environmental protection, safety, excellent application prospect, good social benefit and high economic benefit.

New functionalized 8-hydroxyquinoline-5-sulfonic acid mesoporous silica (HQS-SBA-15) as an efficient catalyst for the synthesis of 2-thiohydantoin derivatives

Mesoporous silica SBA-15 functionalized with 8-hydroxyquinoline-5-sulfonic acid (HQS-SBA-15) was used as a new recyclable nanocatalyst for the one-pot synthesis of 2-thiohydantoin derivatives under solvent-free conditions. The catalyst exhibited excellent recyclability at least for 3 times with a high catalytic activity.

D-Penicillamine and L-cysteine derived thiazolidine catalysts: an efficient approach to both enantiomers of secondary alcohols

D-Penicillamine derived thiazolidine ligands were prepared in a two-step synthetic sequence and used in the enantioselective alkylation of a variety of aromatic aldehydes with diethylzinc at room temperature. Excellent ee, up to >99%, and nearly complete conversions were observed. Structurally analogous L-cysteine derived thiazolidine ligands were also synthesized and tested for comparative purposes, resulting in very good, albeit slightly lower selectivities, up to 89%. The combined use of these two types of thiazolidines constitutes a very interesting strategy for synthesizing both (S) and (R) enantiomers of chiral secondary alcohols, thus leading the way to a myriad of useful optically active products with opposite absolute configurations.

Thiazolidine esters: New potent urease inhibitors

A variety of esters of thiazolidine-4-caboxylic acid were synthesized and investigated for their urease inhibitory properties. A significant increase in urease inhibitory activities of these ester derivatives has been observed. The order of activity increases from methyl ester to heptyl ester but further prolongation of the alkyl chain was proved to be detrimental for receptor binding. These findings provide evidence that the nature of the alkyl chain has a significant impact on the coordination of thiazolidine esters with bi-metallic nickel center of urease. It was also observed that inhibition potentiated by lower pH and with increase in time.

Modular chiral thiazolidine catalysts in asymmetric aryl transfer reactions

Modular chiral thiazolidine derivatives were synthesized in a single step from inexpensive and commercially available starting materials. These ligands catalyzed enantioselective arylation of different aldehydes using aryl boronic acids as a source of transferable aryl groups. The products were obtained in excellent yields and good enantioselectivities.

Conversion of isomeric 2:3 adducts (aminoacid-formaldehyde) to N-acyl-pseudoprolines derivatives

Reaction of acyl chlorides or acid anhydrides with isomeric 2:3 adducts derived from condensation of l-serine (1a), l-threonine (1b) and l-cysteine (1c) methyl esters with formaldehyde afforded N-acyl-pseudoprolines 7-19 in various yields. These 2:3 adducts can be considered as synthetic equivalents of oxaproline and thiaproline moieties. The present work revealed the versatile behaviour of the two 2:3 adducts as a consequence of the ring-chain tautomerism occurring in the five- and/or seven-membered rings.

The relative catalytic efficiency of β-lactamase catalyzed acyl and phosphyl transfer

Phosphonamidates which bear a simple resemblance to penicillin type structures have been synthesised as potential inhibitors of β-lactamases: -ethyl N-(benzyloxycarbonyl) amidomethyl phosphonyl amides, PhCH2OCONHCH2P(O)(OEt)NR2, the amines HNR2 being L-proline, D-proline, L-thiazolidine, and o-anthranilic acid. The proline derivatives completely and irreversibly inactivated the class C β-lactamase from Enterobacter cloacae P99, in a time-dependent manner, indicative of covalent inhibition. The inactivation was found to be exclusive to the class C enzyme and no significant inhibition was observed with any other class of β-lactamase. The anthranilic acid derivative exhibited no appreciable inactivation of the β-lactamases. The phosphonyl proline and phosphonyl thioproline derivatives were separated into their diastereoisomers and their individual second order rate constants for inhibition were found to be 7.72 ± 0.37 and 8.3 × 10-2 ± 0.004 M-1 s-1 for the L-proline derivatives, at pH 7.0. The products of the inhibition reaction of each individual diastereoisomer, analyzed by electrospray mass spectroscopy, indicate that the more reactive diastereoisomers phosphonylate the enzyme by P-N bond fission with the elimination of proline. Conversely, gas chromatographic detection of ethanol release by the less reactive proline diastereoisomer suggests phosphonylation occurs by P-O bond fission. The enzyme enhances the rate of phosphonylation with P-N fission by at least 106 compared with that effected by hydroxide-ion. The pH dependence of the rate of inhibition of the β-lactamase by the more reactive diasteroisomer is consistent with the reaction of the diprotonated form of the enzyme, EH2, with the inhibitor, I (or its kinetic equivalents EH with IH). This pH dependence and the rate enhancement indicate that the enzyme appears to use the same catalytic apparatus for phosphonylation as that used for hydrolysis of β-lactams. The stereochemical consequences of nucleophilic displacement at the phosphonyl centre are discussed.

The steric effect and enantioselectivity of chiral 2,2-disubstituted thiaprolinol derivatives as ligands for borane reduction of aromatic ketones and for diethylzinc addition to aromatic aldehydes

A new series of chiral amino alcohols 3a-e has been prepared from natural amino acid L-cysteine. These compounds have been used as chiral ligands for borane reduction of ketones and for diethylzinc addition to aldehydes. In the reduction of ketones, 3b-e have been used as the substitute of (R)-prolinol to provide (S)-alcohols in good yields had modest enantioselectivity (30-50% ee). In the diethylzinc addition to aldehydes, 3b-e promoted the formation of (S)-alcohols in excellent yields and medium to good enantioselectivities (60-80% ee). Copyright (C) 1996 Published by Elsevier Science Ltd.