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

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

Uses

Used in Pharmaceutical Industry:
Trans-4-Phenyl-L-proline is utilized as a key component in the synthesis of pharmaceuticals, particularly for the development of drugs aimed at treating a variety of medical conditions. Its incorporation into drug molecules can enhance their efficacy and selectivity, making it an indispensable tool in medicinal chemistry.
Used as a Chiral Building Block in Organic Synthesis:
In the field of organic chemistry, trans-4-Phenyl-L-proline is employed as a chiral building block, crucial for the preparation of a diverse range of chemical compounds. Its asymmetric center allows for the creation of enantiomerically pure products, which is vital for the synthesis of biologically active molecules with specific pharmacological properties.
Used in the Development of Biologically Active Compounds:
Due to its phenyl group, trans-4-Phenyl-L-proline is used as a starting material for creating compounds with targeted biological activities. This makes it a valuable asset in the design and synthesis of new molecules with potential therapeutic applications, further expanding its utility in drug discovery and development processes.

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 
• 3973-63-5 5-phenylpiperidin-2-one 
• 99854-36-1 3,3-dichloro-5-phenyl-piperidin-2-one 
• 103290-39-7 (2S,4S)-1-(tert-butoxycarbonyl)-4-phenyl-2-pyrrolidinecarboxylic acid 
• 82087-66-9 N-(benzyloxycarbonyl)-3,4-dehydro-4-phenyl-L-proline 
• 78464-03-6 N-(benzyloxycarbonyl)-cis-4-hydroxy-trans-4-phenyl-L-proline 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 103290-38-6 C₁₇H₂₂NO₇S^(1-)*Li⁽¹⁺⁾ 
• 1356352-00-5 C₂₀H₂₉NO₄ 
• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 
• 35418-16-7 L-t-butyl pyroglutamate 
• 120851-71-0 (2S,4S)-1-Benzoyl-4-phenyl-pyrrolidine-2-carboxylic acid 

Downstream Products

• 113949-55-6 (2S,4S)-1-{2-[Ethoxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-4-phenyl-pyrrolidine-2-carboxylic acid 
• 113949-56-7 trans-1-{[hydroxy(4-phenylbutyl)phosphinyl]acetyl}-4-phenyl-L-proline 
• 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 

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.

Discovery of a novel class of potent and orally bioavailable sphingosine 1-phosphate receptor 1 antagonists

A series of subtype selective sphingosine 1-phosphate receptor 1 (S1P 1) antagonists are disclosed. Our high-throughput screening campaign revealed hit 1 for which an increase in potency and mouse oral exposure was achieved with minor modifications to the chemical scaffold. In vivo efficacy revealed that at high doses compounds 12 and 15 inhibited tumor growth. Further optimization of our lead series led to the discovery of proline derivatives 37 (XL541) and 38 which had similar efficacy as our first generation analogues at significantly lower doses. Analogue 37 displayed excellent pharmacokinetics and oral exposure in multiple species.

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.

LITHIUM DIPHENYLCUPRATE REACTIONS WITH 4-TOSYLOXY-L-PROLINES; AN INTERESTING STEREOCHEMICAL OUTCOME. A SYNTHESIS OF TRANS-4-PHENYL-L-PROLINE.

The reaction of lithium diphenylcuprate with trans-4- and cis-4-tosyloxy-L-prolines gives excellent yields of 4-phenyl substituted L-prolines and the reaction proceeds with net retention of configuration at the carbon center bearing the tosyloxy group.

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