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
• Article Data: 7

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

General Description

(R)-methyl 2-oxothiazolidine-4-carboxylate is a chemical compound with the molecular formula C5H7NO3S and a molar mass of 161.18 g/mol. It is a derivative of thiazolidine, containing a substituent at the 4-position. (R)-methyl 2-oxothiazolidine-4-carboxylate is used in organic synthesis as a reagent for the preparation of various pharmaceuticals and agrochemicals. It has also been investigated for its potential pharmacological properties, including anti-inflammatory and antioxidant effects. Additionally, (R)-methyl 2-oxothiazolidine-4-carboxylate has applications in the food industry, where it is used as a flavoring agent and preservative. Overall, this chemical has diverse uses and is an important building block in the synthesis of various biologically active compounds.

Upstream product

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

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.

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.