1-(1-Oxobutyl)-L-proline

Base Information

• Chemical Name: 1-(1-Oxobutyl)-L-proline
• CAS No.: 23500-13-2
• Molecular Formula: C9H15NO3
• Molecular Weight: 185.223
• Hs Code.: 2933990090
• European Community (EC) Number: 245-696-9
• Nikkaji Number: J228.980F
• Mol file: 23500-13-2.mol

Synonyms:1-(1-Oxobutyl)-L-proline;L-Proline, 1-(1-oxobutyl)-;N-butyryl-l-proline;(S)-N-butanoylproline;SCHEMBL7052375;PNRXXKVCHJXHPZ-ZETCQYMHSA-N;AKOS010373997;NS00051048

Chemical Property of 1-(1-Oxobutyl)-L-proline

Chemical Property:

• Vapor Pressure: 8.96E-07mmHg at 25°C
• Refractive Index: 1.508
• Boiling Point: 378.5 °C at 760 mmHg
• Flash Point: 182.7 °C
• PSA: 57.61000
• Density: 1.185 g/cm³
• LogP: 0.80000
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 185.10519334
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

98%Min ^*data from raw suppliers

1-Butyrylproline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)N1CCCC1C(=O)O
• Isomeric SMILES: CCCC(=O)N1CCC[C@H]1C(=O)O

Technology Process of 1-(1-Oxobutyl)-L-proline

There total 8 articles about 1-(1-Oxobutyl)-L-proline 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: 93.0%

(S)-benzyl 1-butyrylpyrrolidine-2-carboxylate (84520-92-3) → (S)-1-butyrylpyrrolidine-2-carboxylic acid (23500-13-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; under 2585.81 - 2844.39 Torr;

DOI:10.1021/jm9016416

Reference yield: 91.0%

(S)-methyl 1-butylpyrrolidine-2-carboxylate → (S)-1-butyrylpyrrolidine-2-carboxylic acid (23500-13-2)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ol302852q

Reference yield: 25.0%

2,5-dioxopyrrolidin-1-yl butyrate (70741-39-8) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (S)-1-butyrylpyrrolidine-2-carboxylic acid (23500-13-2)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; for 5h; Reflux;

DOI:10.1016/j.tet.2012.10.104

upstream raw materials:

(S)-benzyl 1-butyrylpyrrolidine-2-carboxylate

H-Pro-OBzl

butyryl chloride

L-proline

Downstream raw materials:

C₂₅H₃₀N₄O₄

Refernces

• 1、 Zhu, Mengyi,Wang, Lijuan,He, Jing. "Repurposing the 3-Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification". supporting information. p. 2030 - 2035. Retrieved 2020/11/30.
• 2、 Muley, Laveena,Baum, Bernhard,Smolinski, Michael,Freindorf, Marek,Heine, Andreas,Klebe, Gerhard,Hangauer, David G.. "Enhancement of hydrophobic interactions and hydrogen bond strength by cooperativity: Synthesis, modeling, and molecular dynamics simulations of a congeneric series of thrombin inhibitors". supporting information; experimental part. p. 2126 - 2135. Retrieved 2010/08/19.