(s)-n-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

Base Information

• Chemical Name: (s)-n-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide
• CAS No.: 96293-17-3
• Molecular Formula: C₂₅H₂₄N₂O₂
• Molecular Weight: 384.478
• Hs Code.: 2933 99 80
• DSSTox Substance ID: DTXSID90359670
• Nikkaji Number: J736.577B
• Wikidata: Q72442851
• Mol file: 96293-17-3.mol

Synonyms:(S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide;NBPBPC cpd

Chemical Property of (s)-n-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

Chemical Property:

• Vapor Pressure: 1.24E-14mmHg at 25°C
• Melting Point: 100-103 °C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 606°Cat760mmHg
• PKA: 13.68±0.70(Predicted)
• Flash Point: 320.3°C
• PSA: 49.41000
• Density: g/cm³
• LogP: 4.53160
• Storage Temp.: Store below +30°C.
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 384.183778013
• Heavy Atom Count: 29
• Complexity: 551

Purity/Quality:

≥95% ^*data from raw suppliers

(S)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)CC2=CC=CC=C2)C(=O)NC3=CC=CC=C3C(=O)C4=CC=CC=C4
• Isomeric SMILES: C1C[C@H](N(C1)CC2=CC=CC=C2)C(=O)NC3=CC=CC=C3C(=O)C4=CC=CC=C4

Technology Process of (s)-n-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

There total 86 articles about (s)-n-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide 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: 95.0%

Ni(II)-(S)-BPB-D-Ala + C23H24N2 (1393107-89-5) → C26H29N3O2 + C26H29N3O2 + (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide (96293-17-3,105024-93-9,105112-33-2)

Guidance literature:

Ni(II)-(S)-BPB-D-Ala; C₂₃H₂₄N₂; With potassium carbonate; In acetonitrile; at 50 ℃; for 8h; Inert atmosphere;

With water; optical yield given as %ee; diastereoselective reaction; Acidic conditions;

DOI:10.1016/j.tetasy.2012.05.022

Reference yield: 95.0%

Ni(II)-(S)-BPB-D-Ala + C13H20N2 (523980-91-8) → C16H25N3O2 + C16H25N3O2 + (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide (96293-17-3,105024-93-9,105112-33-2)

Guidance literature:

Ni(II)-(S)-BPB-D-Ala; C₁₃H₂₀N₂; With potassium carbonate; In acetonitrile; at 50 ℃; for 5h; Inert atmosphere;

With water; optical yield given as %ee; diastereoselective reaction; Acidic conditions;

DOI:10.1016/j.tetasy.2012.05.022

Reference yield: 95.0%

1-phenylmethylpiperazine (2759-28-6) + Ni(II)-(S)-BPB-D-Ala → (S)-2-amino-3-(4-benzylpiperazin-1-yl)propionic acid (1393107-98-6) + (R)-2-amino-3-(4-benzylpiperazin-1-yl)propionic acid + (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide (96293-17-3,105024-93-9,105112-33-2)

Guidance literature:

1-phenylmethylpiperazine; Ni(II)-(S)-BPB-D-Ala; With potassium carbonate; In acetonitrile; at 25 ℃; for 0.333333h; Inert atmosphere;

With water; optical yield given as %ee; diastereoselective reaction; Acidic conditions;

DOI:10.1016/j.tetasy.2012.05.022

upstream raw materials:

benzyl chloride

2N-(prolyl)aminobenzophenone

N-benzyl-L-proline

(2-aminophenyl)(phenyl)methanone

Downstream raw materials:

(2R,3S)-phenylserine

(2R;3R)-2-amino-3-hydroxy-3-phenylpropionic acid

(2R,3S)-2-amino-3-hydroxy-3-(o-fluorophenyl)propanoic acid

(S)-2-amino-3-hydroxy-3-methylbutanoic acid

Refernces

• 1、 Craig, Austin,Kolks, Niklas,Urusova, Elizaveta A.,Zischler, Johannes,Brugger, Melanie,Endepols, Heike,Neumaier, Bernd,Zlatopolskiy, Boris D.. "Preparation of labeled aromatic amino acids: Via late-stage18F-fluorination of chiral nickel and copper complexes". supporting information. p. 9505 - 9508. Retrieved 2020/09/03.
• 2、 Watson, Morag E.,Jamieson, Craig,Kennedy, Alan R.,Mason, Andrew M.. "A reappraisal of the Ni-[(Benzylprolyl)amino]benzophenone complex in the synthesis of α,α-disubstituted amino acid derivatives". . . Retrieved 2019/08/08.