5817-26-5

Basic information

• Product Name: ethyl (2S)-pyrrolidine-2-carboxylate
• Synonyms: (-)-L-Proline ethyl ester;L-proline ethyl ester;Proline ethyl ester;(S)-Ethyl pyrrolidine-2-carboxylate;ethyl (2S)-pyrrolidine-2-carboxylate
• CAS NO: 5817-26-5
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.19
• Mol File: 5817-26-5.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 83°C/17mmHg(lit.)
• Flash Point: 69.5°C
• Appearance: /
• Density: 1.031g/cm³
• Vapor Pressure: 0.519mmHg at 25°C
• Refractive Index: 1.4480 to 1.4520
• PKA: 8.23±0.10(Predicted)
• CAS DataBase Reference: ethyl (2S)-pyrrolidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2S)-pyrrolidine-2-carboxylate(5817-26-5)
• EPA Substance Registry System: ethyl (2S)-pyrrolidine-2-carboxylate(5817-26-5)

Safety Data

• Hazardous Substances Data: 5817-26-5(Hazardous Substances Data)

Usage

General Description

Ethyl (2S)-pyrrolidine-2-carboxylate is a chemical compound found in the pyrrolidine family. The "2S" in its name signifies its stereospecific configuration, meaning it has a specific arrangement of atoms in three-dimensional space. It is also referred to as an ester because it features a carbonyl adjacent to an ether, linking two different organic substances—namely, ethyl and pyrrolidine-2-carboxylate. Generally, this chemical is utilized in the production of pharmaceuticals or other organic compounds. As with any chemicals, adequate safety measures must be taken during its handling and usage.

InChI:InChI=1/C7H13NO2/c1-2-10-7(9)6-4-3-5-8-6/h6,8H,2-5H2,1H3/t6-/m0/s1

Upstream product

• 955-40-8 N-benzyl-L-proline ethyl ester 
• 33305-75-8 L-proline ethyl ester monohydrochloride 
• 147-85-3 L-proline 
• 64-17-5 ethanol 

Downstream Products

• 96145-91-4 L-5-Oxo-1,4-diazabicyclo<4.3.0>nonane 
• 101685-19-2 N-Benzeneselenenyl-(S)-proline ethyl ester 
• 135505-96-3 p-Nitrophenoxy S-methyl <(2S)-2-(carbethoxy)-pyrrolidinyl>phosphorothioate 
• 135505-96-3 p-Nitrophenoxy S-methyl <(2S)-2-(carbethoxy)-pyrrolidinyl>phosphorothioate 
• 76638-01-2 (S)(-)-N-(cyclohexene-1-carbonyl)proline 
• 124096-49-7 (S)-1-((E)-2-Phenyl-propenyl)-pyrrolidine-2-carboxylic acid ethyl ester 
• 76076-42-1 (S)-2-Benzyloxymethyl-1-((Z)-3-phenyl-but-2-enyl)-pyrrolidine 
• 63742-09-6 1-((E)-2-methyl-3-phenyl-acryloyl)-L-proline 
• 135112-36-6 Z-Arg(NO₂)-Pro-OEt 
• 955-40-8 N-benzyl-L-proline ethyl ester 
• 128402-38-0 (S)-1-[(E)-2-(2-Allyloxy-phenyl)-propenyl]-pyrrolidine-2-carboxylic acid ethyl ester 
• 24738-82-7 (S)-1-Cyclohex-1-enyl-pyrrolidine-2-carboxylic acid ethyl ester 
• 75230-06-7 (S)-1-[(Z)-2,3-Dibromo-4,4-bis-(4-ethyl-phenyl)-but-2-enoyl]-pyrrolidine-2-carboxylic acid ethyl ester 
• 89218-24-6 (S)-1-((S)-Ethoxy-phenylsulfanylmethyl-phosphinoyl)-pyrrolidine-2-carboxylic acid ethyl ester 

Relevant articles and documents

Dichloromethane as Reactant in Synthesis: An Expedient Transformation of Prolinamide to a Novel Pyrroloimidazolone

-

Stereospecific Synthesis of 3,4-Dihydro-2 H-naphtho-1,4-oxazin-2-ones by Unification of Benzoxepine-4-carboxylates with Chiral Amino Acid Ethyl Esters

A novel and efficient stereocontrolled method has been developed for the preparation of chiral 3,4-dihydro-2H-naphtho[1,2-b][1,4]oxazin-2-ones by the reaction of benzoxepine-4-carboxylates with chiral amino acid ethyl esters for the first time. The chiral 3,4-dihydro-2H-naphtho-1,4-oxazinones have been achieved in one step by the formation of C-N, C-C, and C-O bonds.

Ionic liquids with methotrexate moieties as a potential anticancer prodrug: Synthesis, characterization and solubility evaluation

The technological utility of active pharmaceutical ingredients (APIs) is enormously improved when they are converted into ionic liquids (ILs). API-ILs possess better aqueous solubility and thermal stability than that of solid-state salt or crystalline drugs. However, many such API-ILs are not biocompatible or biodegradable. In the current study, we synthesized a series of IL-APIs using methotrexate (MTX), a potential anticancer prodrug, and biocompatible IL-forming cations (choline and amino acid esters). The MTX-IL moieties were characterized through 1H NMR, FTIR, p-XRD, DSC and thermogravimetric analysis. The solubility of the MTX-ILs was evaluated in simulated body fluids (phosphate-buffered saline, simulated gastric, and simulated intestinal fluids). An assessment of the in vitro antitumor activity of the MTX-ILs in a mammalian cell line (HeLa cells) was used to evaluate their cytotoxicity. The MTX-ILs showed aqueous solubility at least 5000 times higher than that of free MTX and two orders of magnitude higher compared with that of a sodium salt of MTX in both water and simulated body fluids. Importantly, a proline ethyl ester MTX prodrug showed similar solubility as the MTX sodium salt but it provided improved in vitro antitumor activity. These results clearly suggest that the newly synthesized API-ILs represent promising potential drug formulations.