127761-77-7

Basic information

• Product Name: (R)-methyl 2-oxothiazolidine-4-carboxylate
• Synonyms: (R)-methyl 2-oxothiazolidine-4-carboxylate
• CAS NO: 127761-77-7
• Molecular Formula: C₅H₇NO₃S
• Molecular Weight: 161.01
• Product Categories: Heterocycles
• Mol File: 127761-77-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-methyl 2-oxothiazolidine-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-methyl 2-oxothiazolidine-4-carboxylate(127761-77-7)
• EPA Substance Registry System: (R)-methyl 2-oxothiazolidine-4-carboxylate(127761-77-7)

Safety Data

• Hazardous Substances Data: 127761-77-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(R)-methyl 2-oxothiazolidine-4-carboxylate is used as a reagent in organic synthesis for the preparation of various pharmaceuticals and agrochemicals. Its unique structure and functional groups make it a valuable building block in the synthesis of biologically active compounds.
Used in Pharmaceutical Industry:
(R)-methyl 2-oxothiazolidine-4-carboxylate is used as an intermediate in the development of new drugs. Its potential pharmacological properties, such as anti-inflammatory and antioxidant effects, make it a promising candidate for the treatment of various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical industry, (R)-methyl 2-oxothiazolidine-4-carboxylate is used as a precursor for the synthesis of various agrochemicals, including pesticides and herbicides. Its ability to form stable derivatives with other compounds contributes to the development of effective and environmentally friendly agrochemicals.
Used in Food Industry as a Flavoring Agent:
(R)-methyl 2-oxothiazolidine-4-carboxylate is used as a flavoring agent in the food industry. Its unique taste and aroma enhance the sensory properties of various food products, providing consumers with a more enjoyable eating experience.
Used in Food Industry as a Preservative:
In addition to its use as a flavoring agent, (R)-methyl 2-oxothiazolidine-4-carboxylate also serves as a preservative in the food industry. Its ability to inhibit the growth of microorganisms helps to extend the shelf life of food products, ensuring their safety and quality for consumers.

Upstream product

• 67-56-1 methanol 
• 19771-63-2 2-oxothiazolidine-4(R)-carboxylic acid 
• 75-44-5 phosgene 
• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 2485-62-3 L-Cysteine methyl ester 
• 201230-82-2 carbon monoxide 
• 124-38-9 carbon dioxide 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 
• 530-62-1 1,1'-carbonyldiimidazole 
• 74124-79-1 di(succinimido) carbonate 

Downstream Products

• 19771-63-2 2-oxothiazolidine-4(R)-carboxylic acid 

Relevant articles and documents

A convenient synthesis of chiral oxazolidin-2-ones and thiazolidin-2-ones and an improved preparation of triphosgene

Oxazolidin-2-ones and thiazolidin-2-ones are conveniently prepared by condensation of L-serine, L-threonine and L-cysteine, respectively with triphosgene. The corresponding methyl esters may be subsequently obtained by quenching the reaction mixture with methanol, without prior need for the isolation of the free acids. An improved procedure for preparation of triphosgene using an internal cooling system is described.

Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides

Here we solve a long-standing challenge of the site-selective modification of secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C-N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation of various functional groups into natural and synthetic molecules.

Visible-Light-Mediated Liberation and In Situ Conversion of Fluorophosgene

The first example for the photocatalytic generation of a highly electrophilic intermediate that is not based on radical reactivity is reported. The single-electron reduction of bench-stable and commercially available 4-(trifluoromethoxy)benzonitrile by an organic photosensitizer leads to its fragmentation into fluorophosgene and benzonitrile. The in situ generated fluorophosgene was used for the preparation of carbonates, carbamates, and urea derivatives in moderate to excellent yields via an intramolecular cyclization reaction. Transient spectroscopic investigations suggest the formation of a catalyst charge-transfer complex-dimer as the catalytic active species. Fluorophosgene as a highly reactive intermediate, was indirectly detected via its next downstream carbonyl fluoride intermediate by NMR. Furthermore, detailed NMR analyses provided a comprehensive reaction mechanism including a water dependent off-cycle equilibrium.

Acceptor-Controlled Transfer Dehydration of Amides to Nitriles

Palladium-catalyzed dehydration of primary amides to nitriles efficiently proceeds under mild, aqueous conditions via the use of dichloroacetonitrile as a water acceptor. A key to the design of this transfer dehydration catalysis is the identification of an efficient water acceptor, dichloroacetonitrile, that preferentially reacts with amides over other polar functional groups with the aid of the Pd catalyst and makes the desired scheme exergonic, thereby driving the dehydration.

Carbon dioxide as a carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas: Scope and limitations

Carbon dioxide can be used as a convenient carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas. The transient carbamate anion generated by treating a primary or secondary amine group in basic media can be activated with phosphorylating agents such as Diphenylphosphoryl azide (DPPA) and Diphenyl chlorophosphate (DPPCl) but also with other types of electrophiles such as SOCl2, TsCl, or AcCl. The intramolecular trapping of the activated carbamate by a hydroxyl group leads to the formation of 2-oxazolidinones or 2-oxazinones in good to excellent yields. This methodology was successfully applied to the synthesis of cyclic ureas up to 7-membered rings from the corresponding diamines.

Total Synthesis of (+)-Latrunculin A, an Ichthyotoxic Metabolite of the Sponge Latrunculia magnifica, and Its C-15 Epimer

Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach.Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, β-keto ester 27, and phosphonium salt 26, which established the conjugated E,Z-diene moiety of 31.The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection.Final lactonization of 47 was carried out using the Mitsunobu protocol.A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.

SYNTHESIS OF BOTH ENANTIOMERS OF 8-AZA-11-DEOXY-10-THIAPROSTAGLANDIN E1

Synthesis of both enantiomers of 8-aza-11-deoxy-10-thiaprostaglandin E1 has been achieved starting from D- and L-cysteine, respectively.