(R)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

Base Information

• Chemical Name: (R)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide
• CAS No.: 105024-93-9
• Molecular Formula: C25H24N2O2
• Molecular Weight: 384.478
• Hs Code.: 2933990090
• UNII: U35H593W95
• DSSTox Substance ID: DTXSID50359671
• Nikkaji Number: J2.010.213F
• Wikidata: Q72440451
• Mol file: 105024-93-9.mol

Synonyms:105024-93-9;(R)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide;(2R)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide;(R)-N-(2-Benzoylphenyl)-1-(phenylmethyl)-2-pyrrolidinecarboxamide;U35H593W95;2-Pyrrolidinecarboxamide, N-(2-benzoylphenyl)-1-(phenylmethyl)-, (2R);2-Pyrrolidinecarboxamide, N-(2-benzoylphenyl)-1-(phenylmethyl)-, (2R)-;(R)-(+)-2-(N-Benzylprolyl)aminobenzophenone;SCHEMBL3471161;UNII-U35H593W95;DTXSID50359671;FD1118;MFCD18910207;AKOS016843353;SS-5152;B5518;CS-0140518;A921947

Chemical Property of (R)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

Chemical Property:

• Melting Point: 101.0 to 105.0 °C
• Boiling Point: 606℃
• PKA: 13.68±0.70(Predicted)
• Flash Point: 320℃
• PSA: 49.41000
• Density: 1.221
• LogP: 4.53160
• Storage Temp.: 2-8°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:

98%,99%, ^*data from raw suppliers

(R)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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 (R)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

There total 99 articles about (R)-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:

(S)-(+)-2-amino-2-methyl-3-hydroxypropanoic acid

(R)-(-)-2-methylserine

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

(R)-threo-(3,4-methylenedioxy)-β-phenylserine

Refernces

• 1、 Li, Linfeng,Chenna, Bala C.,Yang, Kai S.,Cole, Taylor R.,Goodall, Zachary T.,Giardini, Miriam,Moghadamchargari, Zahra,Hernandez, Elizabeth A.,Gomez, Jana,Calvet, Claudia M.,Bernatchez, Jean A.,Mellott, Drake M.,Zhu, Jiyun,Rademacher, Andrew,Thomas, Diane,Blankenship, Lauren R.,Drelich, Aleksandra,Laganowsky, Arthur,Tseng, Chien-Te K.,Liu, Wenshe R.,Wand, A. Joshua,Cruz-Reyes, Jorge,Siqueira-Neto, Jair L.,Meek, Thomas D.. "Self-Masked Aldehyde Inhibitors: A Novel Strategy for Inhibiting Cysteine Proteases". . p. 11267 - 11287. Retrieved 2021.
• 2、 Quitterer, Felix,Beck, Philipp,Bacher, Adelbert,Groll, Michael. "The formation of pyrroline and tetrahydropyridine rings in amino acids catalyzed by pyrrolysine synthase (PylD)". . p. 8150 - 8153. Retrieved 2014.
• 3、 Kawamura, Akie,Moriwaki, Hiroki,R?schenthaler, Gerd-Volker,Kawada, Kosuke,Ace?a, José Luis,Soloshonok, Vadim A.. "Synthesis of (2S,3S)-β-(trifluoromethyl)-α,β-diamino acid by Mannich addition of glycine Schiff base Ni(II) complexes to N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine". . p. 67 - 72. Retrieved 2015.
• 4、 Belokon', Yu. N.,Chernoglazova, N. I.,Bakhmutov, V. I.,Garbalinskaya, N. S.,Belikov, V. M.. "ASYMMETRIC SYNTHESIS OF α-METHYLAMINOACIDS BY THE ALKYLATION OF GLYCINE, ALANINE, AND PHENYLALANINE IN CHIRAL Ni(II) COMPLEXES". . p. 2595 - 2601. Retrieved 1987.
• 5、 Soloshonok, Vadim A.,Cai, Chaozhong,Hruby, Victor J.,Van Meervelt, Luc. "Asymmetric synthesis of novel highly sterically constrained (2S,3S)-3- methyl-3-trifluoromethyl- and (2S,3S,4R)-3-trifluoromethyl-4- methylpyroglutamic acids". . p. 12045 - 12058. Retrieved 1999.
• 6、 Zhang, Fan,Sun, Hengzhi,Song, Zhuang,Zhou, Shuxi,Wen, Xiaoan,Xu, Qing-Long,Sun, Hongbin. "Stereoselective synthesis of arylglycine derivatives via palladium-catalyzed α-arylation of a chiral nickel(II) glycinate". . p. 4459 - 4464. Retrieved 2015.
• 7、 Vuong, Wayne,Mosquera-Guagua, Fabricio,Sanichar, Randy,McDonald, Tyler R.,Ernst, Oliver P.,Wang, Lei,Vederas, John C.. "Synthesis of Chiral Spin-Labeled Amino Acids". supporting information. p. 10149 - 10153. Retrieved 2019/12/24.