Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate

Bezeichnung:Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate

CAS-Nr144689-93-0

Englisch Name:Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate

CBNumberCB4151009

SummenformelC12H20N2O3

Molgewicht240.3

MOL-Datei144689-93-0.mol

Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate physikalisch-chemischer Eigenschaften

Schmelzpunkt	98-100°C
Siedepunkt	456.2±35.0 °C(Predicted)
Dichte	1.131±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,2-8°C
Löslichkeit	Chloroform, Ethyl Acetate, Methanol
Aggregatzustand	Solid
pka	11.61±0.10(Predicted)
Farbe	Pale Yellow
InChI	InChI=1S/C12H20N2O3/c1-5-7-8-13-9(11(15)17-6-2)10(14-8)12(3,4)16/h16H,5-7H2,1-4H3,(H,13,14)
InChIKey	KZBJJAFGNMRRHN-UHFFFAOYSA-N
SMILES	C1(CCC)NC(C(OCC)=O)=C(C(O)(C)C)N=1
CAS Datenbank	144689-93-0(CAS DataBase Reference)

Sicherheit

HS Code

2933.29.9000

Gefahreninformationscode (GHS)

Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Pale Yellow Solid
Verwenden
An Olmesartan (O550000) intermediate.
Application
Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate is a synthetic drug with pharmacological properties that are similar to those of the natural product medoxomil. It has been shown to be a potent blocker of the GABA receptor and is used for the treatment of epilepsy.It has been shown to be an inhibitor of rat liver microsomes and also has a high affinity for the enzyme cilexetil, which is responsible for the conversion of cilexetil into its active form.
Synthese
To a solution of MeMgCl(55.86 g, 0.74 mol) in tetrahydrofuran was added a solution of diethyl 2-propyl imidazole- 4,5-dicarboxylate (50 g,0.19 mol) in tetrahydrofuran (200 ml) at -10 to 0°C under N2 atmosphere. The mixture was stirred at -5 to 0°C for 10 minutes. The reaction mass was quenched into 400 ml 25 % ammonium chloride solution, followed by extraction with ethyl acetate (300 ml). The organic phase was separated, washed with brine, dried over Na2SO4, and concentrated in vacuo to give Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate, which was crystallized using diisopropyl ether. Yield: 85-90 %.
Definition
Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate is a crucial intermediate for the synthesis of olmesartan medoxomil, which can be produced via the reaction of diethyl 2-propyl-imidazole-4,5-dicarboxylate, the raw material, with methylmagnesium bromide, followed by the acidification with saturated ammonium chloride solution.
Hazard
Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate is sensitive to the skin and may cause allergic skin reactions. It is irritating to the skin and eyes and may also cause respiratory irritation. It is poisonous to aquatic organisms.

Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate Upstream-Materialien And Downstream Produkte

Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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