73401-53-3

Usage

Uses

Used in Pharmaceutical Industry:
(3R)-Thiomorpholinecarboxylic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and properties make it a valuable component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, (3R)-Thiomorpholinecarboxylic acid is utilized as a precursor in the production of agrochemicals. Its incorporation into these products can enhance their effectiveness in agricultural applications, such as pest control and crop protection.
Used as Antibacterial Agent:
(3R)-Thiomorpholinecarboxylic acid is used as an antibacterial agent due to its reported potential to inhibit the growth of certain bacteria. This property can be harnessed in the development of new antimicrobial treatments and products.
Used as Antifungal Agent:
Similarly, (3R)-Thiomorpholinecarboxylic acid has been reported to possess antifungal properties, making it a candidate for use in antifungal applications. This can be particularly beneficial in the development of treatments for fungal infections and in agricultural settings to protect crops from fungal diseases.

InChI:InChI=1/C5H9NO2S/c7-5(8)4-3-9-2-1-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1

Upstream product

• 113494-28-3 (S)-2-Benzyloxycarbonylamino-3-(2-chloro-ethylsulfanyl)-propionic acid benzyl ester 
• 85955-36-8 (S)-2-amino-3-<(2-hydroxyethyl)sulfanyl>propanoic acid 
• 65527-54-0 2-(R)-thiomorpholine carboxylic acid hydrochloride 
• 56674-34-1 (S)-2-amino-3-<(2-chloroethyl)sulfanyl>propanoic acid hydrochloride 
• 98069-36-4 (S)-2-Amino-3-(2-chloro-ethylsulfanyl)-propionic acid 

Relevant academic research and scientific papers

Synthesis of four stereoisomers of 1,4-thiazane-3-carboxylic acid 1-oxide via the asymmetric transformation (combined isomerization-preferential crystallization) of 1,4-thiazane-3-carboxylic acid

In order to synthesize four stereoisomers of 1,4-thiazane-3-carboxylic acid 1-oxide (TCA SO), (S)-1,4-thiazane-3-carboxylic acid [(S)-TCA], which is one of the precursors, was prepared by the asymmetric transformation (combined isomerization-preferential crystallization) of (RS)-TCA. This asymmetric transformation was used (2R, 3R)-tartaric acid [(R)-TA] as a resolving agent and salicylaldehyde as the epimerization catalyst in propanoic acid at 110°C to afford a salt of (S)-TCA with (R)-TA in 100% de with a yield of over 90%. Optically pure (S)-TCA was obtained by treating the salt with triethylamine in methanol in a yield of over 80%, based on (RS)-TCA as the starting material. In addition, asymmetric transformation of (R)-TCA gave (S)-TCA in a yield of 60-70%. (S)-TCA was oxidized by hydrogen peroxide in dilute hydrochloric acid to selectively crystallize (1S, 3S)-TCA SO. (1R, 3S)-TCA-SO of 70% de from the filtrate was allowed to form a salt with (R)-TA after a treatment with triethylamine to give (1R, 3S)-TCA·SO as a single diastereoisomer. (1R, 3R)- and (1S, 3R)-TCA·SO were also prepared by starting from (R)-TCA that had been synthesized from L-cysteine.

Synthesis of Optically Active 1,4-Thiazane-3-carboxylic Acid via Optical Resolution by Preferential Crystallization of (RS)2-Amino-3-[(2-chloroethyl)sulfanyl]propanoic Acid Hydrochloride

Optically active 1,4-thiazane-3-carboxylic acid [TCA] was synthesized from cysteine via optical resolution by preferential crystallization. The intermediate (RS)-2-amino-3-[(2-chloroethyl)sulfanyl]propanoic acid hydrochloride [(RS)-ACS-HCl] was found to exist as a conglomerate based on its melting point, solubility and IR spectrum. (RS)-ACS·HCl was optically resolved by preferential crystallization to yield (R)- and (S)-ACS·HCl. (R)- and (S)-ACS·HCl thus obtained were recrystallized from a mixture of hydrochloric acid and 2-propanol, taking account of the solubility of (RS)-ACS·HCl, efficiently yielding both enantiomers in optically pure forms. (R)- and (S)-TCA were then respectively synthesized by the cyclization of (R)- and (S)-ACS·HCI in ethanol in the presence of triethylamine.