6038-19-3

Basic information

• Product Name: DL-Homocysteinethiolactone hydrochloride
• Synonyms: d,l-homocysteinthiolaktonchlorid;dihydro-3-amino-,hydrochloride,(+-)-2(3h)-thiophenon;hctlhydrochloride;DL-homocysteine thiolactone Hydrocholoride;DL-HOMOCYSTEIN THIOLACTONE HCL; 3-Aminodihydro-2-(3H)-thiophenone Hydrochlorid;(-3-Amino-dihydro-thiophen-2-one Hydrochloride;HOMOCYSTEINE THIOLACTONE HCL, DL-(RG)
• CAS NO: 6038-19-3
• Molecular Formula: C₄H₇NOS*ClH
• Molecular Weight: 153.63
• EINECS: 227-923-3
• Product Categories: Amino Acids;Heterocyclic Compounds;Amines;Heterocycles;Sulfur & Selenium Compounds;Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks;Thiophenes
• Mol File: 6038-19-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 202 °C (dec.)(lit.)
• Boiling Point: 253.8 °C at 760 mmHg
• Flash Point: 107.3 °C
• Appearance: White/Fine Crystalline Powder
• Density: 0.862 g/cm3
• Vapor Pressure: 0.0179mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Water Solubility: 740.5 g/L (20 C)
• Merck: 14,4734
• BRN: 3562103
• CAS DataBase Reference: DL-Homocysteinethiolactone hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Homocysteinethiolactone hydrochloride(6038-19-3)
• EPA Substance Registry System: DL-Homocysteinethiolactone hydrochloride(6038-19-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: XN1928400
• F: 1-8-9
• Hazardous Substances Data: 6038-19-3(Hazardous Substances Data)

Usage

Description

DL-Homocysteinethiolactone hydrochloride is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals. It is a derivative of the amino acid homocysteine, featuring a thiolactone ring and a hydrochloride salt form, which contributes to its reactivity and stability in chemical processes.

Uses

Used in Pharmaceutical Industry:
DL-Homocysteinethiolactone hydrochloride is used as a chemical intermediate for the production of [specific pharmaceuticals] for [reasons related to its chemical properties or reactivity].
Specifically, it is utilized in the synthesis of:
1. Erdosteine:
DL-Homocysteinethiolactone hydrochloride is used as a precursor in the synthesis of erdosteine, a mucolytic agent used for the treatment of respiratory conditions such as chronic obstructive pulmonary disease (COPD) and acute exacerbations of bronchitis. Its role in the synthesis process is crucial for the development of this therapeutic agent.
2. Citiolone:
Additionally, DL-Homocysteinethiolactone hydrochloride serves as an intermediate in the production of citiolone, a compound with potential applications in pharmaceutical formulations. Its involvement in the synthesis of citiolone highlights its versatility and importance in the development of various medicinal compounds.

InChI:InChI=1/C4H7NOS.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m1./s1

Upstream product

• 1120-77-0 D-homocysteine thiolactone hydrochloride 
• 31828-68-9 L-homocysteine thiolactone hydrochloride 
• 1051970-96-7 S-HCT madelate 
• 454-29-5 2-amino-4-mercaptobutyric acid 
• 61540-11-2 3-Methyl-2-oxo-tetrahydrothiophen 
• 462-10-2 DL-homocystine 
• 1195-16-0 N-acetyl-DL-homocysteinethiolactone 

Downstream Products

• 60175-95-3 1,3-thiazane-4-carboxylic acid 
• 53199-57-8 S-(3-deazaadenosyl)-DL-homocysteine 
• 94775-86-7 2-amino-4-<3-(2-methoxyphenoxy)propylthio>butyric acid 
• 454-29-5 2-amino-4-mercaptobutyric acid 
• 94776-12-2 2-amino-4-<2-(2-methoxyphenoxy)ethylthio>butyric acid 
• 84611-22-3 N-chloroacetylhomocysteine thiolactone 
• 192310-93-3 [(S)-1-(2-Oxo-tetrahydro-thiophen-3-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 192310-92-2 (S)-N-(2-Oxo-tetrahydro-thiophen-3-yl)-3-phenyl-2-(3-phenyl-propionylamino)-propionamide 
• 166451-25-8 α-(o-azido)benzoylamino-γ-butyrothiolactone 
• 60084-72-2 2-Amino-4-(12-methyl-benzo[a]anthracen-7-ylmethylsulfanyl)-butyric acid 

Relevant articles and documents

Preparation Method for Homocystein Thiolactone or Selenolactone

The present invention provides an expensive reagent such as homocysteine thiolactone or selenolactone as the main intermediate of erdosteine, or an expensive reagent such as HI. More specifically, A) a homoserine lactone or N - protected homoserine is reacted with a thiocarboxylic acid metal salt or selenocarboxylic acid metal salt (RCOXM, X=S or Se). B) Step A) of producing homocysteine thiolactone or homocysteine sonoactone by deprotection of N - protected homocysteine thiolactone or N - protected homocysteine seleactone. The present invention relates to a method for producing homocysteine thiactone or homocysteine senolactone or a salt thereof by the following reaction scheme. [Reaction Scheme] Then, this time. X Is S or Se, R and R ' are independently alkyl or aryl which is C1 - C6, and M is Na or K.

DL-homocysteine thiolactone hydrochloride and preparation method and applications thereof

The invention belongs to the technical field of medicine, and specifically relates to DL-homocysteine thiolactone hydrochloride and a preparation method and applications thereof. The synthesis methodof DL-homocysteine thiolactone hydrochloride comprises following steps: taking 2-methyl-4-chlorobutyryl chloride as the raw material to prepare an intermediate; distilling the intermediate, collectingdistillate; mixing the distillate with iodine and ammonia water to carry out reactions; and finally re-crystallizing and purifying the reaction product to obtain DL-homocysteine thiolactone hydrochloride. According to the synthesis method, 2-methyl-4-chlorobutyryl chloride is taken as the raw material to prepare DL-homocysteine thiolactone hydrochloride; and the preparation method has the advantages of low cost, small environmental pressure, safe and convenient production, and high yield, and is suitable for large scale production.

Process for the resolution of homocysteine-thiolactone

The present invention relates to a process for the preparation of enantiomerically pure homocysteine-γ-thiolactone comprising optical resolution of racemic homocysteine-γ-thiolactone (I) with a chiral organic acid wherein one isomer is recovered as diastereomeric salt with the organic acid and the other isomer remaining in the mother liquor is submitted to racemisation with a catalytic amount of an aromatic aldehyde and submitted again to optical resolution with the same chiral organic acid.