26839-76-9

Usage

Uses

Used in Pharmaceutical Industry:
(+)-1-(tert-butylamino)-3-[(4-morpholino-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol is used as a pharmaceutical agent for its potential therapeutic effects. The compound's unique structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, (+)-1-(tert-butylamino)-3-[(4-morpholino-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol serves as a valuable compound for studying its chemical properties and reactivity. Its unique structure can provide insights into the development of new synthetic methods and the understanding of reaction mechanisms.
Used in Material Science:
(+)-1-(tert-butylamino)-3-[(4-morpholino-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol can be utilized in material science as a component in the development of new materials with specific properties. Its unique molecular structure may contribute to the creation of materials with enhanced performance characteristics, such as improved stability or reactivity.
Used in Drug Delivery Systems:
Similar to gallotannin, (+)-1-(tert-butylamino)-3-[(4-morpholino-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol can be employed in drug delivery systems to enhance the bioavailability and therapeutic outcomes of various drugs. Its unique chemical properties may allow for the development of novel drug carriers and delivery methods, improving the efficacy of existing treatments.
Chemical Properties:
The compound (+)-1-(tert-butylamino)-3-[(4-morpholino-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol is characterized by its oil-like properties, which may influence its solubility, stability, and reactivity in various chemical reactions and applications. This information is crucial for understanding its potential uses and limitations in different industries.

InChI:InChI=1/C13H24N4O3S/c1-13(2,3)14-8-10(18)9-20-12-11(15-21-16-12)17-4-6-19-7-5-17/h10,14,18H,4-9H2,1-3H3/t10-/m1/s1

Upstream product

• 29023-48-1 timolol 
• 30165-97-0 3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole 
• 67843-74-7 (S)-epichlorohydrin 
• 75-64-9 tert-butylamine 
• 58827-68-2 4-{4-[(2R/S)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine 

Relevant academic research and scientific papers

Process for preparing R-(+)-3-morpholino-4-(3- tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazole

The present invention provides a process for preparing optically active timolol. The process comprises the following steps. Firstly, reacting 3-hydroxy-4-morpholino-1,2,5-thiadiazole with an optically active epichlorohydrin in the presence of a solvent system, which has a first volume and a catalyst optionally in the presence of a suitable base to obtain an optically active intermediate product. Secondly, treating the optically active intermediate product with a solution, which has a second volume and comprises tert-butylamine to obtain an optically active timolol. The solvent system used in the first step can be an amide solvent, sulfoxide solvent, cyclic hydrocarbon solvent, ketone solvent, or a heterocyclic solvent. The catalyst used in the first step can be an alkali metal hydroxide, alkali metal carbonate, alkali metal hydrogen carbonate, piperidine, pyridine, triethylamine, potassium hydroxide, sodium hydroxide, potassium carbonate, and other heterocyclic bases.

Chiral separations of some β-adrenergic agonists and antagonists on AmyCoat column by HPLC

Sixteen β-adrenergic antagonists namely acebutalol, alprenolol, atenolol, bisoprolol, bopindolol, bufurolol, carazolol, celiprolol, indenolol, metaprolol, nebivolol, oxprenolol, practolol, propranolol, tertalol, and timolol, and two β-adrenergic agonists namely cimeterol and clenbuterol were resolved on AmyCoat (150 x 46 mm, 3 μm size of silica particle) by using (85:15:0.1, v/v/v), (90:10:0.1, v/v/v), and (95:05:0.1, v/v/v) combinations of η-heptane, ethanol, and diethylamine solvents, respectively. The flow rates used were 0.5, 1.0, 2.0, and 3.0 ml/min with detection at 225 nm. The values of capacity, separation, and resolution factors ranged from 0.38 to 19.70, 1.08-2.33, and 1.0 and 4.50, respectively. The maximum and minimum resolutions were achieved for celiprolol and bufurolol, respectively. The chiral recognition mechanisms were also discussed. The values of validation parameters were calculated.

Biocatalytic asymmetric synthesis of (S)- and (R)-Timolol

A new biocatalytic route for the synthesis of both enantiomers of Timolol (1) is described. Starting from 3,4-dichloro-1,2,5-thiadiazole (2), (R)- and (S)-Timolol (87% ee) were obtained in 35% and 30% overall yield, respectively. Asymmetric reduction of the intermediate haloketone 5 with baker's yeast afforded the corresponding halohydrin 6 in the optically active form (87% ee), which gave the R enantiomer (distomer) of Timolol. The S enantiomer (eutomer) was obtained via inversion of configuration of the halohydrin following the Mitsunobu procedure.

An improved process of separation of R- and S-timolol

Diastereomeric timolol tartrates 4 are obtained in a one-pot synthesis from the racemic base 2 and optically active O,O-diacetyl- or O,O,- dibenzoyltartaric anhydrides 3, as only one of the diastereomers precipitates from acetone solution. Acidic hydrolysis as the corresponding 4 leads to timolol in high yield and optical purity.