(R)-Metomidate

Base Information

• Chemical Name: (R)-Metomidate
• CAS No.: 61045-91-8
• Molecular Formula: C13H14N2O2
• Molecular Weight: 230.266
• UNII: NUP88P9UDR
• DSSTox Substance ID: DTXSID60209931
• Nikkaji Number: J239.447B
• Wikidata: Q27285064
• ChEMBL ID: CHEMBL406437
• Mol file: 61045-91-8.mol

Synonyms:(R)-Metomidate;(+)-METOMIDATE;61045-91-8;Metomidate, (R)-;Metomidate, (+)-;NUP88P9UDR;methyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylate;methyl (R)-1-(1-phenylethyl)-1H-imidazole-5-carboxylate;1H-Imidazole-5-carboxylic acid, 1-((1R)-1-phenylethyl)-, methyl ester;1H-Imidazole-5-carboxylic acid, 1-(1-phenylethyl)-, methyl ester, (R)-;Etomidate EP Impurity B;UNII-NUP88P9UDR;CHEMBL406437;SCHEMBL4377172;DTXSID60209931;MFCD17012643;Q27285064;methyl 1-[(1r)-1-phenylethyl]-1h-imidazole-5-carboxylate;(r)-(+)-methyl 1-(1-phenylethyl)-1h-imidazole-5-carboxylate

Chemical Property of (R)-Metomidate

Chemical Property:

• PSA: 44.12000
• LogP: 2.27900
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Sparingly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 230.105527694
• Heavy Atom Count: 17
• Complexity: 264

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)N2C=NC=C2C(=O)OC
• Isomeric SMILES: C[C@H](C1=CC=CC=C1)N2C=NC=C2C(=O)OC
• Uses: Methyl (R)-1-(1-Phenylethyl)-1H-imidazole-4-carboxylate is used in the synthesis of Etomidate analogues which are selective inhibitors of steroid 11β-?hydroxylation in the adrenal cortex.

Technology Process of (R)-Metomidate

There total 5 articles about (R)-Metomidate 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: 71.0%

methanol (67-56-1) + etomidate (33125-97-2,56649-47-9) → (R)-Metomidate (61045-91-8)

Guidance literature:

With sodium methylate; at 20 ℃; for 5h;

DOI:10.1021/jm800012w

Reference yield:

(S)-1-phenylethanol (1445-91-6) + 1H-imidazole-5-carboxylic acid methyl ester (17325-26-7) → (R)-Metomidate (61045-91-8) + (S)-Metomidate

Guidance literature:

With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 2h; Title compound not separated from byproducts;

DOI:10.1007/s00706-004-0242-2

Reference yield:

(S)-1-phenylethanol (1445-91-6) + 1H-imidazole-5-carboxylic acid methyl ester (17325-26-7) → (R)-Metomidate (61045-91-8)

Guidance literature:

With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 17h;

DOI:10.1016/j.nucmedbio.2018.11.002

upstream raw materials:

Metomidate

(S)-1-phenylethanol

1H-imidazole-5-carboxylic acid methyl ester

methanol

Downstream raw materials:

(R)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid2-fluoroethyl ester

(R)-(+)-1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid

Refernces

• 1、 -. "Anesthetic compounds and related methods of use". Page/Page column 51. . Retrieved 2015/11/09.
• 2、 Hammerschmidt, Friedrich,Simov, Biljana Peric,Schmidt, Susanne,Schneider, Sabine,Zolle, Ilse. "Chemoenzymatic synthesis of stannylated metomidate as a precursor for electrophilic radiohalogenations - Regioselective alkylation of methyl 1H-imidazole-5-carboxylate [1]". . p. 229 - 239. Retrieved 2007/10/03.