23500-15-4

Basic information

• Product Name: (2S)-1-[2-Methylpropanoyl]-pyrrolidine-2-carboxylic Acid
• Synonyms: (2S)-1-[2-Methylpropanoyl]-pyrrolidine-2-carboxylic Acid;Captopril EP IMpurity E;L-1-Isobutyrylproline;1-Isobutyryl-L-proline;Captopril impurity E;(S)-1-isobutyrylpyrrolidine-2-carboxylic acid;Captopril Impurity R
• CAS NO: 23500-15-4
• Molecular Formula: C₉H₁₅NO₃
• Molecular Weight: 185.2203
• Mol File: 23500-15-4.mol

Chemical Properties

• Melting Point: 122.6-123.7℃
• Boiling Point: 369.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.182±0.06 g/cm3(Predicted)
• PKA: 3.71±0.20(Predicted)
• CAS DataBase Reference: (2S)-1-[2-Methylpropanoyl]-pyrrolidine-2-carboxylic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-1-[2-Methylpropanoyl]-pyrrolidine-2-carboxylic Acid(23500-15-4)
• EPA Substance Registry System: (2S)-1-[2-Methylpropanoyl]-pyrrolidine-2-carboxylic Acid(23500-15-4)

Safety Data

• Hazardous Substances Data: 23500-15-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-1-[2-Methylpropanoyl]-pyrrolidine-2-carboxylic Acid is used as an impurity in the production of Captopril, an ACE inhibitor that is utilized for the treatment of hypertension and heart failure. Its presence in the manufacturing process is crucial for quality control and ensuring the purity of the final product.
Used in Neuroprotective Applications:
(2S)-1-[2-Methylpropanoyl]-pyrrolidine-2-carboxylic Acid is used as a neuroprotective agent, potentially offering protective effects on the nervous system. Its role in this application is due to its structural similarities with Captopril, which is known to have neuroprotective properties.
Used in Neuroresearch:
(2S)-1-[2-Methylpropanoyl]-pyrrolidine-2-carboxylic Acid is used as a neuroresearch product, aiding scientists in understanding the mechanisms of action and potential therapeutic applications of Captopril and other related compounds. Its unique properties may provide insights into the development of new drugs and therapies for neurological disorders.

Upstream product

• 62571-86-2 captopril 
• 33305-75-8 L-proline ethyl ester monohydrochloride 
• 79-31-2 isobutyric Acid 
• 177747-23-8 (S)-methyl 1-(isobutyryl)pyrrolidine-2-carboxylate 

Downstream Products

• 916262-78-7 2-[(4-nitrophenyl)sulfanyl]ethyl N-(2-methyl-1-oxopropyl)-L-prolinate 
• 916262-77-6 2-[(4-nitrophenyl)sulfonyl]ethyl N-(2-methyl-1-oxopropyl)-L-prolinate 
• 916262-63-0 2-oxo-2-phenylethyl N-(2-methyl-1-oxopropyl)-L-prolinate 
• 916262-65-2 2-oxo-2-phenylethyl N-(2-methyl-1-thioxopropyl)-L-prolinate 
• 916262-67-4 2-oxo-2-phenylethyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate 
• 916262-72-1 prop-2-enyl N-{2-[((2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxopentyl)amino]-2-methyl-1-oxopropyl}-L-prolinate 
• 916262-73-2 2-oxo-2-phenylethyl N-{2-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-phenyl-1-oxopropyl)amino]-2-methyl-1-oxopropyl}-L-prolinate 

Relevant articles and documents

Preparation method of aromatic ether compound

The invention discloses a preparation method of an aromatic ether compound. The preparation method comprises the following steps: c) in a solvent, in the presence of a catalyst and alkali, performinga reaction on a compound V with a compound 6 to obtain a compound VII, wherein the definition of each group in the chemical formula is as shown in the specification, and the solvent is a solvent system having two or more elements selected from the group consisting of water, tetrahydrofuran, 2-methyltetrahydrofuran, ethyl acetate, and dioxane. According to the preparation method of the aromatic ether compound, the conversion rate of the reaction can be greatly improved, so that the yield of the step and the total yield of the whole reaction route can be improved; after-treatment and purification operations for preparing the compound VII are greatly simplified, and the compound VII with very high purity can be obtained only by simply filtering a reaction solution and washing and drying a filter cake. The preparation method is suitable for industrial scale-up production.

Novel series of highly potent non-peptide growth hormone secretagogues with improved bioavailability

The discovery and the SAR of acylproline derivatives as highly potent growth hormone secretagogues (GHSs) with good oral bioavailability are described. One representative compound, N-[3-(2,2-dimethylpropylamino)-2-hydroxypropyl]-2(R)-[1-(2,2-dimethylpropionyl)pyrrolidine-2(S)- carbonylamino]-3-naphthalen-2-ylpropionamide (4e), showed potent GHS activity (ED50=1 nM) and good oral bioavailability (BA=33.2%). Moreover, the optically pure N-[3-(2,2-dimethylpropylamino)-2(S)-hydroypropyl]-2(R)-[1-(2,2-dimethylpropionyl)pyrrolidine-2(S)-carbonylamino]-3-naphthalen-2- ylpropionamide ((2S)-4e) showed a good metabolic stability against in vitro clearance (human liver microsome) with potent GHS activity.

Novel N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinates as Aib-Pro synthons

The syntheses of phenacyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate and allyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate are reported. Reactions of these 2H-azirin-3-amine derivatives with Z-protected amino acids have shown them to be suitable synthons

Photochemical desulfurization of thiols and disulfides

A visible light-induced desulfurization process for thiols and disulfides using triethylphosphite and triethylborane is reported. The reaction can be effected on a range of organic molecules having either primary, secondary or tertiary thiol groups and disulfides without the need of protecting groups. Thus, after treating L-cystine 7, L-cystine dimethylester 8, thioctic amide 9 and glutathione disulfide 10, first with tributylphosphine, later with triethylborane/triethylphosphite under irradiation in a one-pot reaction, the corresponding desulfurized compounds L-Ala, L-Ala, 1-octanamide and γ-L-Glu-L-Ala-Gly, respectively, are prepared in high yields with retention of configuration.