(S)-Mephenytoin

Base Information

• Chemical Name: (S)-Mephenytoin
• CAS No.: 70989-04-7
• Molecular Formula: C12H14 N2 O2
• Molecular Weight: 218.255
• Hs Code.: 29332100
• European Community (EC) Number: 621-693-1
• UNII: D9818430MW
• DSSTox Substance ID: DTXSID7046126
• Nikkaji Number: J428.022I
• Wikidata: Q27276264
• Metabolomics Workbench ID: 144178
• ChEMBL ID: CHEMBL1743264
• Mol file: 70989-04-7.mol

Synonyms:(S)-Mephenytoin;70989-04-7;S-Mephenytoin;(S)-(+)-Mephenytoin;(5s)-5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione;Mephenytoin, (+)-;(S)-5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione;Mephenytoin, D-;(+)-Mephenytoin;(+)-Mesantoin;(+)-S-Mephenytoin;d-Mephenytoin;(5S)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione;DTXSID7046126;UNII-D9818430MW;D9818430MW;NCGC00160394-01;DTXCID5026126;CAS-70989-04-7;MFCD00270025;(S)-5-Ethyl-3-methyl-5-phenylhydantoin;MEPHENYTOIN, (S)-;SCHEMBL21768;CHEMBL1743264;BDBM21361;HY-B1184A;(S)-(+)-Mephenytoin, 98%;C(Nc1ccc(Cl)cc1)c2ccc(C)cc2;CHEBI:179062;EX-A6720;Tox21_111783;Tox21_111783_1;NCGC00160394-02;NCGC00165924-04;CS-0102758;A13366;C20130;S10442;(+)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN;(S)-(+)-Mephenytoin, solid, >=98% (HPLC);A934834;EN300-10845170;Q27276264;2,4-Imidazolidinedione, 5-ethyl-3-methyl-5-phenyl-, (5S)-;2,4-Imidazolidinedione, 5-ethyl-3-methyl-5-phenyl-, (S)-

Chemical Property of (S)-Mephenytoin

Chemical Property:

• Melting Point: 135-138 °C
• PKA: 8.07±0.70(Predicted)
• PSA: 49.41000
• Density: 1.154g/cm³
• LogP: 1.74020
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 310

Purity/Quality:

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

(S)-Mephenytoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1(C(=O)N(C(=O)N1)C)C2=CC=CC=C2
• Isomeric SMILES: CC[C@@]1(C(=O)N(C(=O)N1)C)C2=CC=CC=C2
• Uses: S-Mephenytoin has been used as a CYP2C19 substrate for the analysis of cytochrome P450 metabolism. S-Mephenytoin has also been used as probe substrates for LC/MS-based analysis of relative activity factor (RAF). (S)-Mephenytoin can be used as an anticonvulsant agent.

Technology Process of (S)-Mephenytoin

There total 7 articles about (S)-Mephenytoin 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:

N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-2-(3-methyl-3-phenylureido)butanamide → S-mephenytoin (70989-04-7) + (-)-Mephenytoin (71140-51-7)

Guidance literature:

N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-2-(3-methyl-3-phenylureido)butanamide; With n-butyllithium; diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;

With chloro-trimethyl-silane; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h; Overall yield = 83 %; Overall yield = 69 mg; enantioselective reaction;

DOI:10.1002/anie.201502569

Reference yield:

2-Isocyanato-2-phenyl-butyronitrile (33875-36-4,75356-38-6,75442-54-5) → S-mephenytoin (70989-04-7)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O / 0 °C

2: 20percent aq. HCl / 0.25 h / Heating

With hydrogenchloride; In water;

DOI:10.1002/ardp.19803130609

Reference yield:

2-(3-methyl-3-phenylureido)butanoic acid → S-mephenytoin (70989-04-7) + (-)-Mephenytoin (71140-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane; water / 20 h / 0 - 20 °C

2.1: diisopropylamine; n-butyllithium; lithium diisopropyl amide / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 - 20 °C

With n-butyllithium; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1002/anie.201502569

upstream raw materials:

mephenytoin

1-(1-Cyano-1-phenyl-propyl)-3-methyl-urea

2-Isocyanato-2-phenyl-butyronitrile

1-(1-Cyano-1-phenyl-propyl)-3-methyl-urea

Downstream raw materials:

(+)-Nirvanol

(+/-)-4'-Hydroxymephenytoin

[14C]-(S)-4'-Hydroxymephenytoin

Refernces

• 1、 Blaschke, Gottfried,Kraft, Horst Peter,Markgraf, Hildegunde. "Chromatographic Resolutions of Racemates, XI. Comparison of Optically Active Polyamides and Cellulose Triacetate". . p. 3611 - 3617. Retrieved 2007/10/02.