L-prolinamide

Base Information

• Chemical Name: L-prolinamide
• CAS No.: 7531-52-4
• Molecular Formula: C5H10N2O
• Molecular Weight: 114.147
• Hs Code.: 29339900
• European Community (EC) Number: 231-397-0
• UNII: VD6PQK9DHG
• DSSTox Substance ID: DTXSID00226268
• Nikkaji Number: J25.973J
• Wikidata: Q27103084
• Metabolomics Workbench ID: 51285
• ChEMBL ID: CHEMBL1222059
• Mol file: 7531-52-4.mol

Synonyms:2-pyrrolidinecarboxamide;prolinamide;prolinamide, (L)-isomer

Chemical Property of L-prolinamide

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.000923mmHg at 25°C
• Melting Point: 97-102 °C
• Refractive Index: 1.4720 (estimate)
• Boiling Point: 303.6 °C at 760 mmHg
• PKA: 16.21±0.20(Predicted)
• Flash Point: 137.4 °C
• PSA: 55.12000
• Density: 1.106 g/cm³
• LogP: 0.25280
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water and ethanol (50 mg/ml).
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 114.079312947
• Heavy Atom Count: 8
• Complexity: 103

Purity/Quality:

min98% ^*data from raw suppliers

L-Prolinamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC1)C(=O)N
• Isomeric SMILES: C1C[C@H](NC1)C(=O)N
• Chemical Composition and Structure: L-Prolinamide is an important intermediate compound used in the synthesis of polypeptides and chiral drugs. It is composed of a proline amino acid unit with an amide functional group.
• Mechanism of Action: L-Prolinamide serves as a chiral ligand in asymmetric catalysis reactions, including Robinson cyclization and Aldol reactions. It participates in various organic transformations as a catalyst or co-catalyst, enhancing reaction rates and product yields.
• Uses: L-Prolinamide derivatives have been evaluated as potential organocatalysts for Aldol reactions. It has also been utilized in enzymatic polymerization to generate immobilized L-Prolinamide, which exhibits catalytic activity in Aldol reactions. Additionally, L-Prolinamide is used as a model compound in solubility studies and as a catalyst in the synthesis of γ-nitroketones.; L-Prolinamide has been synthesized in high yields without using complicated chemistry or expensive chemicals, highlighting its importance as a readily available intermediate compound in organic synthesis.
• Production Methods: L-Prolinamide is synthesized from L-proline through a series of chemical reactions, including esterification and ammonolysis. It is produced on an industrial scale using proline as the raw material.
• Analysis Method: Liquid chromatography has been developed as an analytical method for detecting L-Prolinamide and its derivatives. This method allows for accurate and sensitive quantification of L-Prolinamide in various samples.

Technology Process of L-prolinamide

There total 30 articles about L-prolinamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Z-Pro-NH2 (34079-31-7,58274-22-9) → L-prolinamide (7531-52-4)

Guidance literature:

With 10% palladium on carbon; hydrogen; In methanol; for 7h;

DOI:10.1016/j.ejmech.2008.12.022

Reference yield: 95.3%

N-acetyl-L-prolinamide (16395-58-7) → L-prolinamide (7531-52-4)

Guidance literature:

With hydrogenchloride; In water; at 103 ℃; for 2h; Temperature;

Reference yield: 91.0%

L-proline methyl ester monohydrochloride (2133-40-6) → L-prolinamide (7531-52-4)

Guidance literature:

With ammonia; In methanol;

upstream raw materials:

methyl (2S)-pyrrolidine carboxylate

ethyl (2S)-pyrrolidine-2-carboxylate

(S)-2-Carbamoyl-pyrrolidine-1-carboxylic acid 2-(4-methoxy-phenyl)-2-oxo-ethyl ester

(S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate

Downstream raw materials:

Z-Pro-NH₂

(S)-2-Aminomethylpyrrolidin

(-)-(S)-1-cyclopropylmethyl-2-pyrrolidinecarboxamide

Z-L-Phe-L-Val-L-Pro-NH₂

Refernces

• 1、 Haar et al.. "-". . p. 4948,4950. Retrieved 1975.
• 2、 -. "Synthesis method of vildagliptin". Paragraph 0031; 0035; 0038; 0042; 0045; 0049. . Retrieved 2020/09/12.
• 3、 Kuranov,Tsypysheva,Khvostov,Zainullina, Liana F.,Borisevich,Vakhitova, Yu.V.,Luzina,Salakhutdinov. "Synthesis and evaluation of camphor and cytisine-based cyanopyrrolidines as DPP-IV inhibitors for the treatment of type 2 diabetes mellitus". . p. 4402 - 4409. Retrieved 2018/07/30.