23037-82-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-ACETYL-PYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER is used as a chiral building block for the synthesis of peptide-based drugs and pharmaceuticals. Its unique structure allows for the creation of novel compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic chemistry, (S)-1-ACETYL-PYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER is used as an intermediate in the production of proline-containing peptides. Its presence in these reactions contributes to the development of new peptide sequences with specific biological activities.
Used in Chemical and Biochemical Research:
(S)-1-ACETYL-PYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER serves as a valuable research tool in chemical and biochemical studies. Its properties and reactivity are investigated to better understand the underlying mechanisms of various chemical reactions and to develop new methodologies in synthetic chemistry.

Upstream product

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

Downstream Products

• 16395-58-7 N-acetyl-L-prolinamide 
• 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 

Relevant academic research and scientific papers

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.

Selective Rhodium-Catalyzed Reduction of Tertiary Amides in Amino Acid Esters and Peptides

Efficient reduction of the tertiary amide bond in amino acid derivatives and peptides is described. Functional group selectivity has been achieved by applying a commercially available rhodium precursor and bis(diphenylphosphino)propane (dppp) ligand together with phenyl silane as a reductant. This methodology allows for specific reductive derivatization of biologically interesting peptides and offers straightforward access to a variety of novel peptide derivatives for chemical biology studies and potential pharmaceutical applications. The catalytic system tolerates a variety of functional groups including secondary amides, ester, nitrile, thiomethyl, and hydroxy groups. This convenient hydrosilylation reaction proceeds at ambient conditions and is operationally safe because no air-sensitive reagents or highly reactive metal hydrides are needed.

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.

Synthesis of quinolactacide via an acyl migration reaction and dehydrogenation with manganese dioxide, and its insecticidal activities

Quinolactacide isolated from Penicillium citrinum F 1539 was synthesized and evaluated for its insecticidal activities. The key steps of the total synthesis were an acyl migration reaction of the enol ester intermediate and dehydrogenation of tetrahydroqu

Enantioselective Carbon-Carbon Bond Formation by Chiral Organotitanium Compounds; Methyltitanium (S)-N-Acylpyrrolidinyl-methoxide Diisopropoxides

New chiral compounds, (S)-N-acylpyrrolidinylmethanols (1b-f and 1h), were synthesized and chiral methyltitanium diisopropoxides (2a-h) were prepared from 1a-h.Enantioselective carbon-carbon bond formation between aromatic carbaldehydes and 2a-h was achieved in yields of 90-97 percent and 10.5-54.1 percent ee.The chiral auxiliaries (1a-h) were recovered in almost quantitative yields without any loss of optical purity.Keywords: (S)-N-acylpyrrolidinylmethanol; carbon-carbon bond formation; enantioselective reaction; methyltitanium diisopropoxide; (R)-1-(1-naphthyl)ethanol; (R)-1-phenylethanol; (S)-prolinol