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
• Article Data: 36

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

Description

N-Boc-4-oxo-L-proline, also known as N-(tert-butoxycarbonyl)-4-oxo-L-proline, is a synthetic organic compound derived from L-proline, an essential amino acid. It features a Boc-protecting group and a 4-oxo (ketone) functional group, which makes it a versatile building block in organic synthesis and a valuable intermediate in the preparation of various pharmaceuticals and bioactive molecules.

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

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

Downstream Products

• 84348-38-9 (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid 
• 401564-36-1 (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester 
• 401566-80-1 tert-butyl (2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidine-1-carboxylate 
• 760937-92-6 3-{(2S,4S)-1-(1,1-dimethylethyloxycarbonyl)-4-[4-(3-methyl-1-phenyl-1H-pyrazole-5-yl)piperazin-1-yl]pyrrolidine-2-ylcarbonyl}thiazolidine 
• 84348-42-5 (2S,4E)-4-benzylidene-N-(t-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 84348-47-0 methyl 4-benzylidene-L-proline hydrochloride 
• 84348-46-9 methyl 4-benzylidene-L-proline hydrochloride 
• 364077-87-2 methyl 4-benzylidene-N-tert-Boc-L-proline 
• 51-35-4 4R-4-hydroxyproline 
• 153790-67-1 N-Boc-D-cis-4-(p-toluenesulfonyloxy)proline 
• 96314-28-2 (2S,4R)-1-(tert-butoxycarbonyl)-4-(tosyloxy)pyrrolidine-2-carboxylic acid 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 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 

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.

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 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.