120806-96-4

Basic information

• Product Name: TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER
• Synonyms: TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER;TRANS-1-BENZOYL-4-HYDROXYL-L-PROLINE METHYL ESTER;N-Benzoylhydroxy-L-prolinmethylester;(2S,4R)-Methyl 4-hydro×y-1-benzoylpyrrolidine-2-carbo×ylate;cis-1-Benzoyl-4-hydro×y-L-prolineMethyl ester;(2S,4R)-Methyl 1-benzoyl-4-hydroxypyrrolidine-2-carboxylate
• CAS NO: 120806-96-4
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.26
• Mol File: 120806-96-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 389.9°Cat760mmHg
• Flash Point: 189.6°C
• Appearance: /
• Density: 1.313g/cm³
• Vapor Pressure: 8.85E-07mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER(120806-96-4)
• EPA Substance Registry System: TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER(120806-96-4)

Safety Data

• Hazardous Substances Data: 120806-96-4(Hazardous Substances Data)

Usage

General Description

TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER is a chemical compound with the molecular formula C17H17NO5. It is a methyl ester derivative of the amino acid hydroxyproline and is often used in the field of pharmaceutical chemistry. TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER is known for its potential therapeutic applications, particularly in the treatment of cardiovascular diseases and as an antioxidant. It is also utilized in the synthesis of various bioactive molecules and pharmaceutical intermediates. The chemical's structural and functional properties make it valuable for research and development in the pharmaceutical industry.

InChI:InChI=1/C13H15NO4/c1-18-12(16)13(17)8-5-9-14(13)11(15)10-6-3-2-4-7-10/h2-4,6-7,17H,5,8-9H2,1H3/t13-/m1/s1

Upstream product

• 98-88-4 benzoyl chloride 
• 67-56-1 methanol 
• 31560-25-5 5-aza-5-benzoyl-2-oxa-3-oxo-bicyclo<2.2.1>heptane 
• 31560-19-7 (2S,4R)-1-benzoyl-4-hydroxy-L-proline 
• 51-35-4 4R-4-hydroxyproline 
• 144-55-8 sodium hydrogencarbonate 
• 2584-71-6 cis-hydroxy-D-proline 
• 114676-47-0 (2R,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester 
• 66831-17-2 (2S,4R)-methyl 4-(benzyloxy)pyrrolidine-2-carboxylate hydrochloride 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 

Downstream Products

• 129155-63-1 N-benzoyl-4-trans-(methanesulfonyloxy)-L-proline 
• 120834-04-0 (2S,4S)-1-Benzoyl-4-fluoro-pyrrolidine-2-carboxylic acid 
• 120806-99-7 (2S,4S)-1-Benzoyl-4-chloro-pyrrolidine-2-carboxylic acid 
• 134003-83-1 tert-butyl (1R,4R)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 
• 134003-84-2 tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 
• 1356446-78-0 fosinopril 
• 103201-78-1 (2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid 
• 96314-26-0 trans-4-phenyl-L-proline 
• 960008-99-5 methyl (2S,4S)-1-(tert-butoxycarbonyl)-4-[3-(methoxycarbonyl)-5-(methylcarbamoyl)-phenoxy]pyrrolidine-2-carboxylate 
• 960008-96-2 methyl (2S,4S)-1-benzoyl-4-[2-bromo-4-(methoxycarbonyl)phenoxy]pyrrolidine-2-carboxylate 
• 960008-92-8 methyl (2S,4S)-1-benzoyl-4-[4-(methoxycarbonyl)phenoxy]pyrrolidine-2-carboxylate 
• 960008-94-0 methyl (2S,4S)-1-benzoyl-4-(2-methoxycarbonyl-4-methylphenoxy)pyrrolidine-2-carboxylate 

Relevant articles and documents

Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands

(-)-Kainic acid potently increases stretch-induced afferent firing in muscle spindles, probably acting through a hitherto uncloned phospholipase D (PLD)-coupled mGlu receptor. Structural modification of (-)-kainic acid was undertaken to explore the C-4 substituent effect on the pharmacology related to muscle spindle firing. Three analogues 1a-c were synthesised by highly stereoselective additions of a CF3, a hydride and an alkynyl group to the Re face of the key pyrrolidin-4-one intermediate 5a followed by further structural modifications. Only the 4-(1,2,3-triazolyl)-kainate derivative 1c retained the kainate-like agonism, increasing firing in a dose-dependent manner. Further modification of 1c by introduction of a PEG-biotin chain on the 1,2,3-triazole fragment afforded compound 14 which retained robust agonism at 1 μM and appears to be suitable for future use in pull-down assays and far western blotting for PLD-mGluR isolation. This journal is

Synthesis of (1R,4R)-2,5-diazabicyclo[2.2.1]heptane derivatives by an epimerization-lactamization cascade reaction

An epimerization-lactamization cascade of functionalized (2S,4R)-4-aminoproline methyl esters is developed and applied in synthesizing (1R,4R)-2,5-diazabicyclo[2.2.1]heptane (DBH) derivatives. (2S,4R)-4-Aminoproline methyl esters are likely to undergo 2-epimerization under basic conditions, followed by an intramolecular aminolysis of the (2R)-epimer to form the bridged lactam intermediates. Key factors identified for this cascade reaction include the electron-withdrawal N-protective group in the substrates and a strong base as the promoter.

Synthetic study of optically active 3-azabicyclo[3.3.0]octane-2,6,8- tricarboxylic acid

Synthesis of (1R,2S,5S,6R,8S)-3-azabicyclo[3.3.0]octane-2,6,8-tricarboxylic acid (2) from trans-4-hydroxy-L-proline (5) was attempted. A Diels-Alder reaction of 3,4-dehydroproline derivative 9 and cyclopentadiene afforded a single stereoisomer 11. The Diels-Alder adduct was smoothly converted to the hydrochloride of 2 (24) via RuO4 oxidation. Although some racemization of the material or product was observed during the synthetic processes, the amino acid 24 proved to be optically pure.