96314-26-0

Basic information

• Product Name: trans-4-Phenyl-L-proline
• Synonyms: (4S)-4-Phenyl-L-proline;trans-4-Phenyl-L-proline;(2S,4S)-4-phenylpyrrolidine-2-carboxylic acid;trans-4-Phenyl-L-proline, (2S,4S)-2-Carboxy-4-phenylpyrrolidine;TRANS-4-PHENYL-L-PROLINE(RS20013976)
• CAS NO: 96314-26-0
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.23
• EINECS: 416-020-1
• Mol File: 96314-26-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: >300 °C (decomp)
• Boiling Point: 372.8 °C at 760 mmHg
• Flash Point: 179.3 °C
• Appearance: /
• Density: 1.186
• Vapor Pressure: 3.22E-06mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: 2-8°C
• PKA: 2.25±0.40(Predicted)
• CAS DataBase Reference: trans-4-Phenyl-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: trans-4-Phenyl-L-proline(96314-26-0)
• EPA Substance Registry System: trans-4-Phenyl-L-proline(96314-26-0)

Safety Data

• Hazard Codes: Xn
• Statements: 43-62
• Safety Statements: 22-36/37
• Hazardous Substances Data: 96314-26-0(Hazardous Substances Data)

Usage

General Description

Trans-4-Phenyl-L-proline is a chemical compound with the molecular formula C11H13NO2. It is a type of proline, which is an amino acid that plays a crucial role in the structure and function of proteins. Trans-4-Phenyl-L-proline is commonly used in the synthesis of pharmaceuticals, particularly in the development of drugs with potential applications in the treatment of various medical conditions. Its chemical structure contains a phenyl group, which makes it useful for creating compounds with specific biological activities. Additionally, trans-4-Phenyl-L-proline has been studied for its potential as a chiral building block in organic synthesis, making it valuable in the preparation of diverse chemical compounds. Overall, this chemical compound has important implications in both the pharmaceutical and chemical industries due to its unique structure and potential biological and synthetic applications.

InChI:InChI=1/C11H13NO2/c13-11(14)10-6-9(7-12-10)8-4-2-1-3-5-8/h1-5,9-10,12H,6-7H2,(H,13,14)/t9?,10-/m0/s1

Upstream product

• 99859-73-1 3-chloro-5-phenyl-piperidin-2-one 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 31560-20-0 (2S,4R)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester 
• 120851-71-0 (2S,4S)-1-Benzoyl-4-phenyl-pyrrolidine-2-carboxylic acid 
• 35418-16-7 L-t-butyl pyroglutamate 
• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 
• 1356352-00-5 C₂₀H₂₉NO₄ 
• 103290-38-6 C₁₇H₂₂NO₇S^(1-)*Li⁽¹⁺⁾ 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 78464-03-6 N-(benzyloxycarbonyl)-cis-4-hydroxy-trans-4-phenyl-L-proline 
• 82087-66-9 N-(benzyloxycarbonyl)-3,4-dehydro-4-phenyl-L-proline 
• 103290-39-7 (2S,4S)-1-(tert-butoxycarbonyl)-4-phenyl-2-pyrrolidinecarboxylic acid 
• 99854-36-1 3,3-dichloro-5-phenyl-piperidin-2-one 

Downstream Products

• 103290-39-7 (2S,4S)-1-(tert-butoxycarbonyl)-4-phenyl-2-pyrrolidinecarboxylic acid 
• 103201-78-1 (2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid 
• 1356446-78-0 fosinopril 
• 113949-56-7 trans-1-{[hydroxy(4-phenylbutyl)phosphinyl]acetyl}-4-phenyl-L-proline 
• 113949-55-6 (2S,4S)-1-{2-[Ethoxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-4-phenyl-pyrrolidine-2-carboxylic acid 

Relevant articles and documents

Preparation methods of antihypertensive Fosinopril sodium and key intermediate thereof

The invention relates to preparation methods of an antihypertensive Fosinopril sodium and a key intermediate thereof trans-4-phenyl-L-proline suitable for industrial production. Synthesis of the key intermediate trans-4-phenyl-L-proline has high chiral selectivity, and the method is simple and easy to operate.

Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines

Analogues of captopril, enalaprilat, and the phosphinic acid [[hydroxy(4-phenylbutyl)phosphinyl]acetyl)-L-proline incorporating 4-substituted proline derivatives have been synthesized and evaluated as inhibitors of angiotensin-converting enzyme (ACE) in vitro and in vivo. The 4-substituted prolines, incorporating alkyl, aryl, alkoxy, aryloxy, alkylthio, and arylthio substituents were prepared from derivatives of 4-hydroxy- and 4-ketoproline. In general, analogues of all three classes of inhibitors with hydrophobic substituents on proline were more potent in vitro than the corresponding unsubstituted proline compounds. 4-Substituted analogues of captopril showed greater potency and duration of action than the parent compound as inhibitors of the angiotensin I induced pressor response in normotensive rats. The S-benzoyl derivative of cis-4-(phenylthio)captopril, zofenopril, was found to be one of the most potent compounds of this class and is now being evaluated clinically as an antihypertensive agent. In the phosphinic acid series, the 4-ethylenethioketal and trans-4-cyclohexyl derivatives were found to be the most potent compounds in vitro and in vivo. A prodrug of the latter compound, fosinopril, is also being evaluated in clinical trials.

Method for making substituted prolines

A method is provided for making substituted prolines of the structure STR1 wherein X is lower alkyl or aryl, R is H, lower alkyl or an alkali metal and Z is an N-protecting group, which method includes the step of reacting a compound of the structure STR2