N-(2-Acetylphenyl)-1-benzyl-L-prolinamide

Base Information

• Chemical Name: N-(2-Acetylphenyl)-1-benzyl-L-prolinamide
• CAS No.: 82704-15-2
• Molecular Formula: C20H22N2O2
• Molecular Weight: 322.407
• DSSTox Substance ID: DTXSID50516505
• Wikidata: Q82377970
• Mol file: 82704-15-2.mol

Synonyms:82704-15-2;N-(2-Acetylphenyl)-1-benzyl-L-prolinamide;DTXSID50516505;(s)-o-(N-benzylprolyl)aminoacetophenone

Chemical Property of N-(2-Acetylphenyl)-1-benzyl-L-prolinamide

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 322.168127949
• Heavy Atom Count: 24
• Complexity: 445

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC=CC=C1NC(=O)C2CCCN2CC3=CC=CC=C3
• Isomeric SMILES: CC(=O)C1=CC=CC=C1NC(=O)[C@@H]2CCCN2CC3=CC=CC=C3

Technology Process of N-(2-Acetylphenyl)-1-benzyl-L-prolinamide

There total 8 articles about N-(2-Acetylphenyl)-1-benzyl-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: 85.0%

Cu(C6H5CH2N(CH2)3CHCONC6H4C(CH3)NCH2CO2) + acetaldehyde (75-07-0,9002-91-9) → C6H5CH2N(CH2)3CHCONHC6H4C(O)CH3 (82704-15-2) + DL-threonine (80-68-2,134357-96-3,7013-32-3,82822-12-6) + rac-allo-threonine (72-19-5,80-68-2,144-98-9,632-20-2,2676-21-3,7004-04-8,24830-94-2,28954-12-3,36676-50-3,134357-96-3,7013-32-3,82822-12-6) + copper(II) sulfide

Guidance literature:

With hydrogenchloride; hydrogen sulfide; sodium methylate; In methanol; to soln. of Cu-complex and MeCHO in anhyd. MeOH methanolic NaOMe added under Ar, kept at 25°C for 1 h, HCl added, diluted with H2O, treated with H2S; filtered, washed with H2O and CHCl3;

DOI:10.1039/c39820000180

Reference yield: 50.0%

2-aminoacetophenone (551-93-9) + (S)-1-benzylpyrrolidine-2-carboxylic acid hydrochloride (92086-93-6) → (S)-o-<(N-benzylprolyl)amino>acetophenone (82704-15-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at -20 ℃; for 2h;

DOI:10.1021/ja00300a030

Reference yield:

acetaldehyde (75-07-0,9002-91-9) + C22H23N3O3(2-)*Cu(2+) → D-Threonine (632-20-2,134357-96-3,7013-32-3,82822-12-6) + D-allo-threonine (24830-94-2,134357-96-3,7013-32-3,82822-12-6) + (S)-o-<(N-benzylprolyl)amino>acetophenone (82704-15-2)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1039/c39820000180

upstream raw materials:

2-aminoacetophenone

(S)-1-benzylpyrrolidine-2-carboxylic acid hydrochloride

acetaldehyde

N-benzyl-(S)-proline chloroanhydride

Downstream raw materials:

D-Threonine

D-allo-threonine

(2S,3S)-2-amino-3-hydroxybutanoic acid

L-threonine

Refernces

• 1、 Belokon', Yu. N.,Zel'tzer, I. E.,Bakhmutov, V. I.,Saporovskaya, M. B.,Ryzhov, M. G.,et al.. "Asymmetric Synthesis of Threonine and Partial Resolution and Retroracemization of α-Amino Acids via Copper(II) Complexes of Their Schiff Bases with (S)-2-N-(N'-Benzylprolyl)aminobenzaldehyde and (S)-2-N-(N'-Benzylprolyl)aminoacetophenone. Crystal and Molecular Structure of a ...". . p. 2010 - 2017. Retrieved 2007/10/02.