84348-37-8

Basic information

• Product Name: N-Boc-4-oxo-L-proline
• Synonyms: (S)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;N-TERT-BOC-4-OXO-L-PROLINE;N-TERT-BUTOXYCABONYL-4-OXO-L-PROLINE;N-T-BOC-4-OXO-L-PROLINE;BOC-L-PRO(4-OXO);BOC-4-OXO-L-PROLINE;N-BOC-4-OXO-L-PROLINE, 97%;(S)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid
• CAS NO: 84348-37-8
• Molecular Formula: C₁₀H₁₅NO₅
• Molecular Weight: 229.23
• Product Categories: pharmacetical;Pharmaceuticalintermediates
• Mol File: 84348-37-8.mol

Chemical Properties

• Melting Point: 160 °C (dec.)
• Boiling Point: 390.8±42.0 °C(Predicted)
• Appearance: /
• Density: 1.304±0.06 g/cm3(Predicted)
• Vapor Pressure: 0.001Pa at 25℃
• Storage Temp.: Store at 0-5°C
• PKA: 3.85±0.20(Predicted)
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: N-Boc-4-oxo-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-4-oxo-L-proline(84348-37-8)
• EPA Substance Registry System: N-Boc-4-oxo-L-proline(84348-37-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 84348-37-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
N-Boc-4-oxo-L-proline is used as a key intermediate in the synthesis of Boc-protected cis-4-trifluoromethyl and cis-4-difluoromethyl-L-prolines. These protected proline derivatives are crucial for the development of novel pharmaceuticals with improved properties, such as enhanced stability, bioavailability, and selectivity towards specific biological targets.
In the field of medicinal chemistry, the Boc-protecting group is commonly employed to shield the amino group of proline during the synthesis of complex molecules, ensuring the desired reactivity and selectivity of the ketone moiety. The subsequent removal of the Boc group under mild acidic conditions allows for the formation of the final product with the desired functional groups intact.
Furthermore, the trifluoromethyl and difluoromethyl substitutions on the proline scaffold can significantly influence the biological activity and pharmacokinetic properties of the resulting compounds. These fluorinated proline analogs have been found to exhibit improved binding affinity, metabolic stability, and selectivity towards various enzymes and receptors, making them attractive candidates for the development of new drugs targeting a wide range of diseases, including cancer, neurological disorders, and infectious diseases.

Upstream product

• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 154456-97-0 2-benzyl 1-(tert-butyl) (S)-4-oxopyrrolidine-1,2-dicarboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 51-35-4 4R-4-hydroxyproline 
• 7664-93-9 sulfuric acid 
• 79-37-8 oxalyl dichloride 
• 331442-12-7 (trans)-1-[(1,1-dimethylethoxy)carbonyl]-4-hydroxy-L-proline 
• 89813-47-8 N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester 
• 147266-92-0 (2R,4S )-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 618-27-9 hydroxy L-proline 
• 34619-03-9 tert-butyldicarbonate 

Downstream Products

• 364078-08-0 4-benzylidene-N-tert-Boc-L-proline 
• 154456-97-0 2-benzyl 1-(tert-butyl) (S)-4-oxopyrrolidine-1,2-dicarboxylate 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 166410-05-5 tert-butyl N^α-Boc-4-keto-L-prolinate 
• 876953-58-1 N-(tert-butyloxycarbonyl)-trans-4-(methylthio)-L-proline 
• 876953-56-9 (2S,4R)-2-[(S)-1-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-4-methylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 96314-28-2 (2S,4R)-1-(tert-butoxycarbonyl)-4-(tosyloxy)pyrrolidine-2-carboxylic acid 
• 153790-67-1 N-Boc-D-cis-4-(p-toluenesulfonyloxy)proline 
• 51-35-4 4R-4-hydroxyproline 
• 364077-87-2 methyl 4-benzylidene-N-tert-Boc-L-proline 
• 84348-46-9 methyl 4-benzylidene-L-proline hydrochloride 
• 84348-47-0 methyl 4-benzylidene-L-proline hydrochloride 

Relevant articles and documents

Altering the sex pheromone cyclo(L-pro-l-pro) of the diatom seminavis robusta towards a chemical probe

As a major group of algae, diatoms are responsible for a substantial part of the primary production on the planet. Pennate diatoms have a predominantly benthic lifestyle and are the most species-rich diatom group, with members of the raphid clades being motile and generally having heterothallic sexual reproduction. It was recently shown that the model species Seminavis robusta uses multiple sexual cues during mating, including cyclo(L-Pro-L-Pro) as an attraction pheromone. Elaboration of the pheromone-detection system is a key aspect in elucidating pennate diatom life-cycle regulation that could yield novel fundamental insights into diatom speciation. This study reports the synthesis and bio-evaluation of seven novel pheromone analogs containing small structural alterations to the cyclo(L-Pro-L-Pro) pheromone. Toxicity, attraction, and interference assays were applied to assess their potential activity as a pheromone. Most of our analogs show a moderate-to-good bioactivity and low-to-no phytotoxicity. The pheromone activity of azide-and diazirine-containing analogs was unaffected and induced a similar mating behavior as the natural pheromone. These results demonstrate that the introduction of confined structural modifications can be used to develop a chemical probe based on the diazirine-and/or azide-containing analogs to study the pheromone-detection system of S. robusta.

Method for synthesizing tert-2-(3- (2S)-4- butyl)-1- ester of n-oxo-isothiazole alkyloxycarbonylpyrrolidinecarboxylic acid (by machine translation)

The technical scheme of the present (2S) - 4 - invention is that the following) - 1 - technical scheme of the present invention, is that the compound is obtained. by the continuous production of the: compound having L - the following beneficial, effects: the Boc compound is obtained II, from the following technical scheme III, No.No. STR3, No.No. IV; The technical proposal of the present invention is the following technical proposal: II No.No. STR3 III. No., No. The following technical II, proposal III Boc - L - of the present, N - Boc - 4 - IV invention is the following (2S) - 4 -) - 1 - technical proposal: No.No. STR8. No. II No.No. :(1) STR8 III, No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2, No.No.No. STR8No.No.No.No. .(2) STR8No., No.No.No.. STR8No., No.No.No., STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR7No.No.No.No. ST (by machine translation)

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.

Industrial production method of teneligptin intermediate

The invention relates to the technical field of biochemical engineering, in particular to an industrial production method of a teneligptin intermediate (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester. The method comprises the following steps: oxidizing a raw material N-Boc-hydroxyproline through an oxidizing agent in the presence of a catalyst; performing quenching with water after reaction ends, singly treating water phase in a waste water treatment pipeline, and concentrating organic phase, so as to obtain a product N-Boc-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester crude product, and performing recrystallization on the crude product through a solvent, so as to obtain a finished product. Compared with the prior art,the industrial production method has the advantages that high-quality (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester can be efficiently and stably produced, the purity is greater than 99 percent, unknown single impurity is smaller than 0.3 percent, and three-waste treatment reach the standards.

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.

Ledipasvir preparation method

The invention discloses a Ledipasvir preparation method. The Ledipasvir preparation method includes steps: (1) Ledipasvir intermediate product 1-LD-B preparation; (2) Ledipasvir intermediate product 2-LD-E preparation; (3) Ledipasvir intermediate product 3-LD-F preparation; (4) Ledipasvir intermediate product 4-LD-J preparation; (5) Ledipasvir intermediate product 5-LD-L preparation; (6) Ledipasvir-LD-Q preparation. The Ledipasvir preparation method has advantages of technical maturity and stability, product quality stability, safety and reliability in production process and suitableness for industrial production.

Preparation method of N-t-butyloxycarboryl-ketone-L-proline

The invention relates to a preparation method of N-t-butyloxycarboryl-ketone-L-proline, and belongs to the technical field of synthesis of drug intermediates. In order to solve the problems that existing reaction is dramatic and low in safety and the product yield stability is low, the invention provides the preparation method of the N-t-butyloxycarboryl-ketone-L-proline. The method comprises thefollowing steps: under the existence of an inorganic alkaline reagent, enabling L-hydroxyproline to react with di-tert-butyl dicarbonate ester in a mixed solvent of water and a water-soluble organic solvent, and removing the organic solvent at the end of the reaction, thereby obtaining a residual aqueous solution containing an intermediate product carboxylate; and under the existence of a TEMPO catalyst, directly generating oxidizing reaction between the obtained intermediate product carboxylate and dihalide isocyanurate, and acidifying a product at the end of the reaction, thus obtaining theproduct N-t-butyloxycarboryl-ketone-L-proline. The preparation method can realize stable reaction, so as to achieve effects of increasing the yield and improving the purity.

Synthesis of 4 - oxo - L - proline derivatives (by machine translation)

The invention relates to the field of preparation methods of chemical drug intermediates, in particular to a method for synthesizing a 4-oxo-L-proline derivative. The method comprises steps as follows: L-hydroxyproline and an oxidant are mixed, and a mixture is obtained and reacts to produce an intermediate product; after an amino-group protective agent is added to a solution containing the intermediate product, the mixture reacts continuously; then, the mixture has a quenching reaction and is subjected to acidification, extraction, separation, drying and purification, and the 4-oxo-L-proline derivative is obtained. According to the method for synthesizing the 4-oxo-L-proline derivative, the primary raw material L-hydroxyproline is low in cost and easy to obtain; the whole synthesizing steps are convenient, simple and easy to operate; poisonous reagents such as heavy metals and the like are not used in the production process, and the 4-oxo-L-proline derivative is environment-friendly, low in cost and suitable for industrial production.

Preparation method for medical intermediate N-Boc-cis-4-hydroxy-L-proline

The invention provides a preparation method for a medical intermediate N-Boc-cis-4-hydroxy-L-proline. The preparation method comprises the following steps: with L-hydroxyproline as a raw material, subjecting the raw material to Boc protection; then carrying out hydroxyl radical oxidation so as to obtain N-Boc-4-oxo-L-proline; dissolving N-Boc-4-oxo-L-proline in a solvent and successively carrying out reduction with a reducing agent and purification at a certain temperature so as to obtain the product N-Boc-cis-4-hydroxy-L-proline. The method has the advantages of good reaction selectivity, high product ee value and low preparation cost.

Method for preparing hydrobromic acid teneligliptin

The invention provides a method for preparing hydrobromic acid teneligliptin. The method includes steps of preparing L-hydroxyproline; mixing the L-hydroxyproline and sodium bicarbonate with each other to obtain mixtures, dissolving the mixtures in water, adding acetone into the water, dropping di-tert-butyl dicarbonate into the water, carrying out room-temperature reaction overnight and then treating reaction products to obtain t-butyloxycarboryl-N-hydroxyproline; preparing t-butyloxycarboryl-N-4-oxo-proline from the t-butyloxycarboryl-N-hydroxyproline; preparing (2S)-4-oxo-2-(3-thiazolidine carbonyl)-1-pyrrolidine carboxylic acid tert-butyl ester from the t-butyloxycarboryl-N-4-oxo-proline; preparing compounds III from compounds IV; preparing compounds II from the compounds III; preparing compounds 1-(3-methyl-1-phenyl-1H-pyrazole-5-base) piperazine from the compounds II; preparing intermediates I; preparing the hydrobromic acid teneligliptin from the intermediates I. The method has the advantages that the method is low in cost, and the cost of the method is only two-thirds of the cost of an existing method in the prior art; the yield of the hydrobromic acid teneligliptin is higher than 95%, and the purity of the hydrobromic acid teneligliptin is higher than 98%.