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

Melting point:

98-100°C

Boiling point:

456.2±35.0 °C(Predicted)

Density 

1.131±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform, Ethyl Acetate, Methanol

form 

Solid

pka

11.61±0.10(Predicted)

color 

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 DataBase Reference

144689-93-0(CAS DataBase Reference)

Safety Information

HS Code 

2933.29.9000

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

Chemical Properties

Pale Yellow Solid

Uses

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.

Synthesis

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(144689-93-0)Related Product Information

• Olmesartan
• Calcitonin salmon
• Olmesartan
• 4-(1-Methoxy-1-methylethyl)-2-propyl-1H-Imidazole-5-carboxylic acid ethyl ester
• OlMesartan Methyl Ester
• 5-[4’-Hydroxymethyl-(1,1’-biphenyl)-2-yl]-1-triphenylmethyltetrazole
• 4-Cloromethyl-5-methyl-1,3-dioxol-2-one
• 2,2'-(2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-4,5-diyl)bis(propan-2-ol)
• 3,6-Dihydro-6,6-diMethyl-2-propyl-3-[[2'-[2-(triphenylMethyl)-2H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]Methyl]-4H-furo[3,4-d]iMidazol-4-one
• OlMesartan MedoxoMil iMpurity V
• N-Trityl Olmesartan Ethyl Ester
• Diethyl 2-propylImidazoledicarbonate
• OlMesartan MedoxoMil Butyl IMpurity
• Olmesartan Impurity 12
• 5-[4'-(Bromomethyl)-[1,1'-biphenyl]-2-yl]-2-(triphenylmethyl)-2H-tetrazole
• 4,5-Dimethyl-1,3-dioxol-2-one
• 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid
• Olmesartan Impurity 10