23037-82-3

Basic information

• Product Name: (S)-1-ACETYL-PYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: (S)-1-ACETYL-PYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER
• CAS NO: 23037-82-3
• Molecular Formula: C₉H₁₅NO₃
• Molecular Weight: 185.2203
• Mol File: 23037-82-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-1-ACETYL-PYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-ACETYL-PYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER(23037-82-3)
• EPA Substance Registry System: (S)-1-ACETYL-PYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER(23037-82-3)

Safety Data

• Hazardous Substances Data: 23037-82-3(Hazardous Substances Data)

Usage

General Description

"(S)-1-acetyl-pyrrolidine-2-carboxylic acid ethyl ester" is a chemical compound with a molecular formula of C9H15NO3. It is an ester derivative of the amino acid proline and is often used in the synthesis of peptide-based drugs and pharmaceuticals. The compound has been studied for its potential as a chiral building block in organic synthesis and as an intermediate in the production of proline-containing peptides. It is typically produced through a multi-step chemical synthesis process and is used as a reagent in organic chemistry reactions. The compound has potential applications in the pharmaceutical industry and is also used as a research tool in chemical and biochemical studies.

Upstream product

• 33305-75-8 L-proline ethyl ester monohydrochloride 
• 75-36-5 acetyl chloride 
• 64-17-5 ethanol 
• 68-95-1 (S)-acetylproline 
• 78-39-7 Triethyl orthoacetate 
• 147-85-3 L-proline 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 

Downstream Products

• 938-54-5 1-ethyl-pyrrolidine-2-carboxylic acid ethyl ester 
• 89311-29-5 8a(S)-6,7,8,8a-tetrahydro-4-methylpyrrolo<1,2-d><1,2,4>triazin-1(2H)-one 
• 928048-89-9 1-aza-3-(2-nitrobenzoyl)bicyclo[3.3.0]octane-2,4-dione 
• 928048-88-8 2-oxo-1-azabicyclo[3.3.0]oct-3-en-4-yl 2-nitrobenzoate 
• 113557-11-2 (S)-N-acetylpyrrolidinyl-1,1-diphenylmethanol 
• 113557-10-1 (S)-N-acetylpyrrolidinyl-1,1-dimethylmethanol 
• 16395-58-7 N-acetyl-L-prolinamide 

Relevant articles and documents

Hydrolysis, polarity, and conformational impact of C-terminal partially fluorinated ethyl esters in peptide models

Fluorinated moieties are highly valuable to chemists due to the sensitive NMR detectability of the 19F nucleus. Fluorination of molecular scaffolds can also selectively influence a molecule's polarity, conformational preferences and chemical reactivity, properties that can be exploited for various chemical applications. A powerful route for incorporating fluorine atoms in biomolecules is last-stage fluorination of peptide scaffolds. One of these methods involves esterification of the C-terminus of peptides using a diazomethane species. Here, we provide an investigation of the physicochemical consequences of peptide esterification with partially fluorinated ethyl groups. Derivatives of N-acetylproline are used to model the effects of fluorination on the lipophilicity, hydrolytic stability and on conformational properties. The conformational impact of the 2,2-difluoromethyl ester on several neutral and charged oligopeptides was also investigated. Our results demonstrate that partially fluorinated esters undergo variable hydrolysis in biologically relevant buffers. The hydrolytic stability can be tailored over a broad pH range by varying the number of fluorine atoms in the ester moiety or by introducing adjacent charges in the peptide sequence.

Concurrent esterification and N-acetylation of amino acids with orthoesters: A useful reaction with interesting mechanistic implications

The concurrent esterification and N-acetylation of amino acids has been studied with triethyl orthoacetate (TEOA) and triethyl orthoformate (TEOF). In a surprising finding, only 1 equiv of TEOA in refluxing toluene was necessary to convert l-proline and l-phenylalanine into the corresponding N-acetyl ethyl esters in good yield. The same transformation using TEOF was not effective. Stereochemical outcome and stoichiometric studies as well as structural variation of the amino acids in this reaction provided unexpected mechanistic insight.

PROLINE-BASED TOPOLOGIC PYRACETAM ANALOGS AND THEIR NOOTROPIC ACTIVITY

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