166410-05-5

Usage

Uses

Used in Pharmaceutical Industry:
BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER is used as a building block for the synthesis of pharmaceuticals. Its stable and protected structure allows for the creation of complex molecules that can be used in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER serves as a key component in the synthesis of various agrochemicals. Its role as a building block contributes to the development of effective and stable products for agricultural applications.
Used in Organic Synthesis:
BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER is utilized as a versatile reagent in organic synthesis. Its stable nature and the presence of the tert-butyl ester group make it suitable for the production of a wide range of fine chemicals and complex organic molecules.

InChI:InChI=1/C10H15NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h7H,4-5H2,1-3H3,(H,13,14)/t7-/m0/s1

Upstream product

• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 75-65-0 tert-butyl alcohol 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 7529-22-8 4-methylmorpholine N-oxide 
• 1634-04-4 tert-butyl methyl ether 
• 51-35-4 4R-4-hydroxyproline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 170850-75-6 BOC-Hyp-OtBu 

Downstream Products

• 1535212-06-6 C₃₁H₄₀F₂N₄O₇ 
• 1201986-55-1 ((R)-3-(4-fluorophenyl)pyrrolidin-1-yl)((2S,4R)-4-(fluorophenyl)pyrrolidin-2-yl)methanone hydrochloride 
• 1201987-30-5 (2S,4R)-tert-butyl 4-(4-fluorophenyl)-2-((R)-3-(4-fluorophenyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate 
• 1201986-76-6 (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-fluorophenyl)-pyrrolidine-2-carboxylic acid 
• 1201986-75-5 (2S,4R)-4-(4-fluorophenyl)-pyrrolidine-2-carboxylic acid 
• 1201986-74-4 (S)-4-(4-fluorophenyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid 
• 860781-14-2 tert-butyl (2S,3S,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate 
• 860781-13-1 tert-butyl (2S,3R,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate 
• 860781-15-3 tert-butyl (2S,4S)-[3,3-²H₂]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate 
• 344286-68-6 tert-butyl N^α-Boc-cis-4-hydroxy-4-phenyl-L-prolinate 

Relevant academic research and scientific papers

Stereoselective synthesis of (3S,4S)-tert-butyl-N-Boc-3-ethyl-4-hydroxy-l- prolinate and (3S,4R)-tert-butyl-N-Boc-3-ethyl-4-hydroxy-l-prolinate

Diastereomers of tert-butyl-N-Boc-3-ethyl-4-hydroxy-l-prolinate 1 and 2 have been synthesized in six steps starting from readily available Boc-protected trans-4-hydroxy-l-proline. The key reactions in the synthesis are asymmetric reductions, firstly on th

Synthesis of 4-(Arylmethyl)proline Derivatives

A synthesis of 4 - (arylmethyl)proline by using Suzuki cross-couplings was developed. The route permits access to a variety of 4-substituted proline derivatives bearing various aryl moieties that expand the toolbox of proline analogues for studies in chemistry and biology.

Synthesis method of teneligliptin-related impurity

The invention discloses a synthesis method of a teneligliptin-related impurity, optimal reaction steps and reaction conditions are screened out through a large number of experiments, the whole processis reasonable in design, high in operability, mild in reaction condition and high in yield, and industrial production can be realized. According to the invention, Boc-L-hydroxyproline and 1-(3-methyl-1-phenyl-5-pyrazolyl)piperazine are taken as raw materials, and the raw materials are subjected to seven-step reaction to synthesize the teneligliptin-related impurity, and the prepared teneligliptin-related impurity is high in purity, can provide a basis for quality control, safety and efficiency evaluation of teneligliptin, and has important application values.

Synthesis technology of N-Boc-4-oxo-L-proline tert-butyl ester

The invention discloses a synthesis technology of N-Boc-4-oxo-L-proline tert-butyl ester, and relates to the technical field of medicine synthesis. The synthesis technology solves the problems that inthe prior art, the production cost is low, the product yield is low, and the synthesis technology is not suitable for industrial production. According to the synthesis technology, Boc anhydride is used to generate tert-butyl carbonate, special esterification reagents namely O-tert-butyl-N,N'-diisopropyl isourea and EDC condensation reagent are not used, and the production cost is reduced by morethan 70%. Sodium hypochlorite is directly used to replace ruthenium tetroxide and chromium trioxide to prepare oxidized hydroxyl and is safe and reliable, furthermore, the post treatment is simple, the environmental pollution is greatly reduced, the operation of the synthesis technology is easy to perform, the technological conditions are easy to control, the synthesis technology is suitable for massive production, and the yield of step three can reach 69% and is higher than that of a conventional technology.

An Unconventional Redox Cross Claisen Condensation-Aromatization of 4-Hydroxyprolines with Ketones

Reaction of α-amino acids, particularly prolines and their derivatives with carbonyl compounds via decarboxylative redox process, is a viable strategy for synthesis of structurally diverse nitrogen centered heterocyclics. In these processes, the decarboxylation is the essential driving force for the processes. The realization of the redox process without decarboxylation may offer an opportunity to explore new reactions. Herein, we report the discovery of an unprecedented redox Claisen-type condensation aromatization cascade reaction of 4-substituted 4-hydroxyproline and its esters with unreactive ketones. We found that the use of propionic acid as a catalyst and a co-solvent can change the reaction course. The commonly observed redox decarboxylation and aldol condensation reactions are significantly minimized. Moreover, unreactive ketones can effectively participate in the Claisen condensation reaction. The new reactivity enables a redox cyclization via an unconventional Claisen-type condensation reaction of in situ formed enamine intermediates from ketone precursors with 4-substituted 4-hydroxyproline and its esters as electrophilic acylation partners. Under the reaction conditions, the cascade process proceeds highly regio- and stereoselectively to afford highly synthetically and biologically valued cis-2,3-dihydro-1H-pyrrolizin-1-ones with a broad substrate scope in efficient 'one-pot' operation, whereas such structures generally require multiple steps.

SYNTHETIC SPHINGOLIPID-LIKE MOLECULES, DRUGS, METHODS OF THEIR SYNTHESIS AND METHODS OF TREATMENT

Small molecules comprised of azacyclic constrained sphingolipid-like compounds and methods of their synthesis are provided. Formulations and medicaments are also provided that are directed to the treatment of disease, such as, for example, neoplasms, canc

Substituted saturated aza heterocycles as inhibitors of nitric oxide synthase

Disclosed herein are compounds of Formula (I) STR1 and pharmaceutically acceptable salts thereof which have been found useful in the treatment of nitric oxide synthase mediated diseases and disorders, including neurodegenerative disorders, disorders of ga

Synthesis of kainoid analogues

4-oxoproline has been used as a chiral template in a synthesis of kainoid analogues which are epimeric with the parent compound at C-3.