L-Proline, 5-oxo-3-[4-(trifluoromethyl)phenyl]-, (3R)-

Base Information

• Chemical Name: L-Proline, 5-oxo-3-[4-(trifluoromethyl)phenyl]-, (3R)-
• CAS No.: 291763-97-8
• Molecular Formula: C12H10F3NO3
• Molecular Weight: 273.212
• DSSTox Substance ID: DTXSID30459547
• Nikkaji Number: J1.336.988G
• Wikidata: Q82283340
• Mol file: 291763-97-8.mol

Synonyms:L-Proline, 5-oxo-3-[4-(trifluoromethyl)phenyl]-, (3R)-;291763-97-8;DTXSID30459547;(2S,3R)-3-(4-Trifluoromethylphenyl)-5-oxo-2-pyrrolidinecarboxylic acid

Chemical Property of L-Proline, 5-oxo-3-[4-(trifluoromethyl)phenyl]-, (3R)-

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 273.06127767
• Heavy Atom Count: 19
• Complexity: 375

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(NC1=O)C(=O)O)C2=CC=C(C=C2)C(F)(F)F
• Isomeric SMILES: C1[C@@H]([C@H](NC1=O)C(=O)O)C2=CC=C(C=C2)C(F)(F)F

Technology Process of L-Proline, 5-oxo-3-[4-(trifluoromethyl)phenyl]-, (3R)-

There total 4 articles about L-Proline, 5-oxo-3-[4-(trifluoromethyl)phenyl]-, (3R)- 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%

C40H36ClF3N4NiO6 → (2S,3R)-3-(p-trifluoromethylphenyl)pyroglutamic acid (291763-97-8)

Guidance literature:

C₄₀H₃₆ClF₃N₄NiO₆; With hydrogenchloride; In methanol; water; at 70 ℃; for 2h;

In water;

DOI:10.1039/c3ob41959b

Reference yield: 85.0%

C35H27F3N4O6(2-)*Ni(2+) → (S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2) + o-[N-(α-picolyl)amino]acetophenone (261768-47-2) + (2S,3R)-3-(p-trifluoromethylphenyl)pyroglutamic acid (291763-97-8)

Guidance literature:

C₃₅H₂₇F₃N₄O₆^(2-)*Ni⁽²⁺⁾; With hydrogenchloride; In methanol; at 70 ℃;

With ammonium hydroxide; In water;

DOI:10.1021/jo0495438

Reference yield:

(S)-4-phenyl-3-{(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoyl}-1,3-oxazolidin-2-one (264626-04-2) → (2S,3R)-3-(p-trifluoromethylphenyl)pyroglutamic acid (291763-97-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DBU / dimethylformamide / 0.5 h / 22 °C

1.2: aq. HCl / methanol

2.1: ammonia

With ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; 1.1: Addition / 1.2: Hydrolysis / 2.1: Cyclization;

DOI:10.1002/1521-3773(20000616)39:12<2172::AID-ANIE2172>3.0.CO;2-0

upstream raw materials:

(S)-4-phenyl-3-{(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoyl}-1,3-oxazolidin-2-one

Downstream raw materials:

(2S,3R)-3-(4-Trifluoromethyl-phenyl)-pyrrolidine-2-carboxylic acid ethyl ester

ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-trifluoromethylphenyl)prolinate

ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-trifluoromethylphenyl)pyroglutamate