33224-01-0

Basic information

• Product Name: TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE
• Synonyms: trans-4-Cotininecarboxylic acid 97%;trans-1-Methyl-4-carboxy-5-(3-pyridyl)-2-pyrrolidinone;TIMTEC-BB SBB003355;TRANS-1-METHYL-2-(3-PYRIDYL)PYRROLIDIN-5-ONE-3-CARBOXYLIC ACID;TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE;TRANS-4-COTININECARBOXYLIC ACID;TRANS-4'-CARBOXYCOTININE;CARBOXY COTININE
• CAS NO: 33224-01-0
• Molecular Formula: C₁₁H₁₂N₂O₃
• Molecular Weight: 220.22
• Product Categories: Building Blocks;C11;Chemical Synthesis;Heterocyclic Building Blocks;Nicotine Derivatives;C9 to C46;Heterocyclic Building Blocks;Pyridines
• Mol File: 33224-01-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 194-195 °C(lit.)
• Boiling Point: 483.8°Cat760mmHg
• Flash Point: 246.4°C
• Appearance: /
• Density: 1.327g/cm³
• Vapor Pressure: 3.6E-10mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 3.94±0.40(Predicted)
• CAS DataBase Reference: TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE(33224-01-0)
• EPA Substance Registry System: TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE(33224-01-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 33224-01-0(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 33224-01-0 differently. You can refer to the following data:
1. A major metabolite of nicotine in humans
2. trans-4-Cotininecarboxylic acid was used in the preparation of cotinine-conjugated horseradish peroxidase during immunoblot analysis. Anion of trans-4-cotininecarboxylic acid has been employed as pyridyl-carboxylate ligand in the preparation of polymeric copper(II) complex.

General Description

Carboxyl group of trans-4-cotininecarboxylic acid (carboxycotinine) can be used for chemical crosslinking.

InChI:InChI=1/C11H12N2O3/c1-13-9(14)5-8(11(15)16)10(13)7-3-2-4-12-6-7/h2-4,6,8,10H,5H2,1H3,(H,15,16)/t8-,10+/m1/s1

Synthetic route

rac trans-4-cotinine carboxylic acid → (2R,3R)-cotinine carboxylic acid + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0)

Conditions	Yield
With ammonium formate In methanol at 20℃; Reagent/catalyst; Solvent; Resolution of racemate;

2-(2-(2-(2-(2-(2-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethanamine (474082-35-4) + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0) → (2S,3S)-N-(29-amino-3,6,9,12,15,18,21,24,27-nonaoxanonacosyl)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxamide

Conditions	Yield
Stage #1: (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide for 0.25h; Sonication; Stage #2: 2-(2-(2-(2-(2-(2-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethanamine In dimethyl sulfoxide for 0.25h; Sonication;	28.9%

diazomethane (186581-53-3, 908094-01-9) + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0) → trans-4'-carboxycotinine methyl ester (33224-03-2)

Conditions	Yield
In acetone at 20℃; for 0.333333h;	39 mg

Fmoc-Val-OH (68858-20-8) + C39H59NO15 + Fmoc-Tyr(tBu)-OH (71989-38-3) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Nα-fluorenyl-9-methoxycarbonyl-D-Met (71989-28-1, 144701-23-5, 112883-40-6) + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6) → W peptide

Conditions

Yield

Stage #1: Nα-fluorenyl-9-methoxycarbonyl-D-Met With 4-methyl-morpholine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; MBHA link amide resin; Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.166667h; MBHA link amide resin; Automated synthesizer; Stage #3: Fmoc-Val-OH; C39H59NO15; Fmoc-Tyr(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl); N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester Further stages;

...Expand

C39H59NO15 + Fmoc-D-Lys(BOC)-OH (92122-45-7) + Nα-fluorenyl-9-methoxycarbonyl-D-Met (71989-28-1, 144701-23-5, 112883-40-6) + N-(9-fluorenylmethoxycarbonyl)-D-valine (84624-17-9) + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0) + Fmoc-D-Tyr(O-tBu)-OH + 1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan → wkymvm-NH2

Conditions

Yield

Stage #1: Nα-fluorenyl-9-methoxycarbonyl-D-Met With 4-methyl-morpholine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; MBHA link amide resin; Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.166667h; MBHA link amide resin; Automated synthesizer; Stage #3: C39H59NO15; Fmoc-D-Lys(BOC)-OH; Nα-fluorenyl-9-methoxycarbonyl-D-Met; N-(9-fluorenylmethoxycarbonyl)-D-valine; (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid; Fmoc-D-Tyr(O-tBu)-OH; 1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan Further stages;

2-(2-(2-(2-(2-(2-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethanamine (474082-35-4) + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0) → (2S,3S)-N-(1-(4-((3-(((S)-4-(3,4-dichlorobenzyl)morpholin-2-yl)methyl)ureido)methyl)phenyl)-1-oxo-5,8,11,14,17,20,23,26,29-nonaoxa-2-azahentriacontan-31-yl)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxamide trifluoroacetic acid salt

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dimethyl sulfoxide / 0.25 h / Sonication 1.2: 0.25 h / Sonication 2.1: O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / dimethyl sulfoxide / 0.5 h / Sonication 2.2: 0.5 h / Sonication View Scheme

Downstream Products

• 33224-03-2 trans-1-Methyl-4-methoxycarbonyl-5-(3-pyridyl)-2-pyrrolidinon 
• 187986-11-4 wkymvm-NH₂ 
• 187986-11-4 W peptide 

Relevant articles and documents

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.