1499-56-5

Basic information

• Product Name: TRANS-4-HYDROXY-L-PROLINE METHYL ESTER
• Synonyms: TRANS-4-HYDROXY-L-PROLINE METHYL ESTER;L-Proline, 4-hydroxy-, methyl ester, (4R)- (9CI);METHYL(2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLATE;L-Proline, 4-hydroxy-, Methyl ester, (4R)-;(2R,4S)-METHYL4-HYDROXYPYRROLIDINE-2-CARBOXYLATE;METHYL (2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLATE(Hydrochloride form);Trans-4-Hydroxy-L-P
• CAS NO: 1499-56-5
• Molecular Formula: C₆H₁₁NO₃
• Molecular Weight: 145.16
• Product Categories: CARBOXYLICESTER;Esters;Pyrrolidines
• Mol File: 1499-56-5.mol
• Article Data: 72

Chemical Properties

• Melting Point: 156-160 °C
• Boiling Point: 247.177°C at 760 mmHg
• Flash Point: 103.289°C
• Appearance: /
• Density: 1.216g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.487
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 14.44±0.40(Predicted)
• CAS DataBase Reference: TRANS-4-HYDROXY-L-PROLINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-4-HYDROXY-L-PROLINE METHYL ESTER(1499-56-5)
• EPA Substance Registry System: TRANS-4-HYDROXY-L-PROLINE METHYL ESTER(1499-56-5)

Safety Data

• Hazardous Substances Data: 1499-56-5(Hazardous Substances Data)

Usage

Description

TRANS-4-HYDROXY-L-PROLINE METHYL ESTER, also known as (2S,4R)-Methyl 4-Hydroxypyrrolidine-2-carboxylate, is an organic compound derived from the esterification of trans-4-hydroxy-L-proline with methanol. It is a white crystalline solid with a molecular formula of C6H11NO3 and is characterized by its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
TRANS-4-HYDROXY-L-PROLINE METHYL ESTER is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly in the preparation of Pyridazinamine derivatives. These derivatives act as modulators of SMARCA2 and BRM target proteins, which play crucial roles in the regulation of gene expression and cellular processes. By modulating these target proteins, Pyridazinamine derivatives have the potential to treat various diseases and disorders related to the dysregulation of these proteins.
Used in Chemical Synthesis:
TRANS-4-HYDROXY-L-PROLINE METHYL ESTER is also used as a versatile building block in the synthesis of various organic compounds, including natural products, pharmaceuticals, and agrochemicals. Its unique chemical structure allows for a wide range of reactions, such as esterification, amidation, and cyclization, making it a valuable starting material for the development of new molecules with diverse applications.

InChI:InChI=1/C6H11NO3/c1-10-6(9)5-2-4(8)3-7-5/h4-5,7-8H,2-3H2,1H3/t4?,5-/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 51-35-4 4R-4-hydroxyproline 
• 67-56-1 methanol 
• 3398-22-9 trans-4-hydroxyproline 
• 75-36-5 acetyl chloride 
• 1063998-64-0 (2S,4R)-4-Hydroxy-pyrrolidine-2-carbonyl chloride 
• 2584-71-6 cis-hydroxy-D-proline 
• 60-29-7 diethyl ether 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 

Downstream Products

• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 5211-24-5 (2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester 
• 1173195-05-5 (2S,4R)-1-Cyclohexylcarbamoyl-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester 
• 129430-93-9 methyl (2S,4R)-4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 122350-59-8 (2S,4R)-1-(9H-fluoren-9-yl)methyl-2-methyl-4-hydroxypyrrolidine-1,2-dicarboxylate 
• 114676-48-1 (2S,4R)-1-benzyl-4-hydroxyproline methyl ester 
• 13135-69-8 (2S,4R)-methyl 4-hydroxy-1-methylpyrrolidine-2-carboxylate 
• 179990-59-1 (2S,4R)-4-hydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 
• 61703-38-6 trans-4-hydroxy-L-proline amide 
• 90965-82-5 Phe-Hyp 
• 64616-75-7 (2S,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid hydrazide 
• 160882-77-9 (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 
• 179990-60-4 (2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 

Relevant articles and documents

BIFUNCTIONAL COMPOUNDS FOR DEGRADING BTK VIA UBIQUITIN PROTEOSOME PATHWAY

The present invention relates to compounds useful for degrading BTK via a ubiquitin proteolytic pathway. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of various disease, conditions, or disorders.

Pyrrolidine ring puckering and prolyl amide bond configurations of 2-methyl-allo-hydroxyproline-based dipeptides

An expeditious method for the synthesis of homo and heterochiral dipeptides containing l-alanine and d/l 2-methyl allo-hydroxyl prolines was developed using direct aminolysis of bicyclic lactones derived from d/l alanine. The impact of C-2 methylation and its spatial orientation on the pyrrolidine ring puckering and prolyl amide bond configuration was ascertained by solution NMR studies. The present studies reveal that C-2 methylation causes the prolyl amide bond to exist exclusively in the trans geometry in both homo- and heterochiral dipeptides. However, the spatial orientation of the C-2 methyl group and its i + 2 position in appropriately capped model dipeptides may nucleate into a turn like structure.

Synthesis method of teneligliptin key intermediate

The invention discloses a synthesis method of a teneligliptin key intermediate, and relates to the technical field of synthesis, in particular to a synthesis method of a teneligliptin key intermediate(2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester. According to the synthesis method, L-hydroxyproline is subjected to an esterification reaction to obtain a compound 1; the compound 1 is protected by t-butyloxycarboryl to obtain a compound 2; the compound 2 is subjected to an oxidation reaction to obtain a compound 3; the compound 3 and thiazolidine are subjected to an ammonia ester exchange reaction to obtain a compound 4. According to the method, a synthesis route suitable for industrial production is designed aiming at the teneligliptin key intermediate,the complexity of the operation is lowered, expensive dehydration reagents are also avoided, the yield is high, the cost is low, and the synthesis method is suitable for industrial application and popularization.