(R)-Licarbazepine

Base Information

• Chemical Name: (R)-Licarbazepine
• CAS No.: 104746-03-4
• Molecular Formula: C15H14N2O2
• Molecular Weight: 254.288
• Hs Code.: 2933990090
• UNII: UQY83V0QWA
• DSSTox Substance ID: DTXSID501346125
• Nikkaji Number: J514.998C
• Wikidata: Q27291213
• ChEMBL ID: CHEMBL313120
• Mol file: 104746-03-4.mol

Synonyms:104746-03-4;(R)-Licarbazepine;R-Licarbazepine;Licarbazepine, (R)-;R-10-Monohydroxy-dihydro-carbamazepin;UNII-UQY83V0QWA;CGP-13698;UQY83V0QWA;(R)-MHD;(5R)-5-hydroxy-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide;(R)-(-)-10,11-Dihydro-10-hydroxy-5H-dibenzo(b,f)azepine-5-carboxamide;5H-Dibenz(b,f)azepine-5-carboxamide, 10,11-dihydro-10-hydroxy-, (10R)-;5H-Dibenz[b,f]azepine-5-carboxamide, 10,11-dihydro-10-hydroxy-, (10R)-;CHEMBL313120;SCHEMBL1744541;BMPDWHIDQYTSHX-CQSZACIVSA-N;CHEBI:174357;DTXSID501346125;AKOS030254382;OXCARBAZEPINE METABOLITE, (R)-MHD;PD132502;(R)-10-Monohydroxy-10,11-dihydro Carbamazepine;J-001241;Q27291213;(R)-(-)-10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide

Chemical Property of (R)-Licarbazepine

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 190-192°C
• Refractive Index: 1.677
• Boiling Point: 431.275 °C at 760 mmHg
• PKA: 13.75±0.20(Predicted)
• Flash Point: 214.628 °C
• PSA: 66.56000
• Density: 1.336 g/cm³
• LogP: 3.25820
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 254.105527694
• Heavy Atom Count: 19
• Complexity: 347

Purity/Quality:

99% ^*data from raw suppliers

(R)-10-Monohydroxy-10,11-dihydroCarbamazepine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2=CC=CC=C2N(C3=CC=CC=C31)C(=O)N)O
• Isomeric SMILES: C1[C@H](C2=CC=CC=C2N(C3=CC=CC=C31)C(=O)N)O
• Recent ClinicalTrials: Disposition of Eslicarbazepine Acetate and Its Metabolites S-licarbazepine and R-licarbazepine
• Uses: An optically active metabolite of carbamazepine. ee=98% [a]d=-193 (C=1, pyridine A metabolite of Eslicarbazepine acetate, (BIA 2-093) a novel central nervous system drug. (R)-10-Monohydroxy-10,11-dihydro Carbamazepine is the metabolite of Oxcarbazepine (OXC) and Eslicarbazepine acetate, (BIA 2-093, ESL), novel central nervous system drugs. ee=98% [α]d=-193 (C=1, py ridine)

Technology Process of (R)-Licarbazepine

There total 23 articles about (R)-Licarbazepine 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:

oxcarbazepine (28721-07-5) → R-licarbazepine (104746-03-4) + S-licarbazepine (104746-04-5)

Guidance literature:

oxcarbazepine; With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In dichloromethane; at -10 - 10 ℃;

With hydrogenchloride; dihydrogen peroxide; In methanol; water;

With sodium hydrogencarbonate; In water;

Reference yield:

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide (29331-92-8) + (3R-trans)-dihydro-2,5-dioxofuran-3,4-diyl diacetate (6283-74-5) → R-licarbazepine (104746-03-4) + S-licarbazepine (104746-04-5)

Guidance literature:

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide; With pyridine; In ethyl acetate; at 25 - 35 ℃; for 0.25h;

(3R-trans)-dihydro-2,5-dioxofuran-3,4-diyl diacetate; In ethyl acetate; at 30 - 35 ℃; for 1h; Overall yield = 77.08 %; Overall yield = 0.7 g; Further stages;

Reference yield:

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide (29331-92-8) → R-licarbazepine (104746-03-4) + S-licarbazepine (104746-04-5)

Guidance literature:

With chiralcel OD-H column; In ethanol; hexane; isopropyl alcohol; at 25 ℃; Resolution of racemate;

DOI:10.1002/chir.22231

upstream raw materials:

oxcarbazepine

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide

licarbazepine methoxyacetate

(10R)-10-[(2S)-(acetyloxy)(phenyl)ethanoate]-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide

Downstream raw materials:

(+)-Licarbazepine acetate

eslicarbazepine acetate

Refernces

• 1、 El-Behairy,Sundby. "One-step lipase-catalysed preparation of eslicarbazepine". . p. 98730 - 98736. Retrieved 2016.
• 2、 -. "Preparation method of anti-epileptic drug eslicarbazepine acetate". . . Retrieved 2017/09/01.