1H-IMidazole-5-carboxylic acid, 4-(1-hydroxy-1-Methylethyl)-2-propyl-1-[[2'-[1-(triphenylMethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]Methyl]-, ethyl ester Chemical Properties

Melting point:

161℃

Boiling point:

889.7±75.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

13.18±0.29(Predicted)

color 

White to Off-White

Water Solubility 

4.6μg/L at 25℃

LogP

9.64 at 25℃

Safety Information

RIDADR 

UN1325

HazardClass 

4.1

1H-IMidazole-5-carboxylic acid, 4-(1-hydroxy-1-Methylethyl)-2-propyl-1-[[2'-[1-(triphenylMethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]Methyl]-, ethyl ester Usage And Synthesis

Uses

Tritylolmesartan Ethyl Ester is an impurity of olmesartan medoxomil (O550000), an angiotensin II receptor antagonist and anti-hypertensive drug.

Synthesis

To ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[4-[2-(tetrazol-5-yl)phenyl]phenyl]methylimidazole-5-carboxylate (BIH, 100 g, 1 eq.) was added dichloromethane (500 mL, 5 vol.), and stirred until completely dissolved. Triethylamine (32.3 mL, 1.1 eq.) was added and the reaction mixture was cooled to 0 °C - 5 °C. A solution of triphenylchloromethane (63.22 g, 1.08 eq.) in dichloromethane (300 mL, 3 vol.) was slowly added dropwise over 30 min at 0 °C-5 °C. After the dropwise addition was completed, the reaction mixture was warmed to 25°C-30°C with continuous stirring for 12 hours. Triphenylchloromethane (2.92 g, 0.05 eq.) was added additionally and stirring was continued for 3 hours. The reaction was monitored by thin layer chromatography (TLC, unfolding agent: 10% methanol/dichloromethane, UV detection) to confirm complete conversion of BIH. The reaction mixture was cooled to 0°C-5°C, demineralized water (270 mL, 2.7 v/v) was added, and stirred at 25°C-30°C for 15 min. Layers were left to separate and the aqueous phase was extracted with dichloromethane (200 mL, 2 volumes). The organic phases were combined and washed with deionized water (500 mL, 5 volumes). The organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure at 40°C-45°C to afford ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[4-[2-(triphenylmethyltetrazol-5-yl)phenyl]phenyl]methylimidazole-5-carboxylate (BIT, 135 g, 89% yield).

References

[1] Patent: EP2891650, 2015, A1. Location in patent: Paragraph 0298-0300
[2] Patent: US2015/239854, 2015, A1. Location in patent: Page/Page column 39

1H-IMidazole-5-carboxylic acid, 4-(1-hydroxy-1-Methylethyl)-2-propyl-1-[[2'-[1-(triphenylMethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]Methyl]-, ethyl ester(144690-33-5)Related Product Information

• 4,5-Bismethylene-1,3-dioxolan-2-one
• OlMesartan Lactone IMpurity
• Olmesartan
• Dehydro Olmesartan
• OlMesartan MedoxoMil Ethyl Methyl Analog
• 5-(4'-Bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole
• Trityl olMesartan acid
• Trityl olMesartan MedoxoMil iMpurity II
• OlMesartan Methyl Ester
• 5-[4’-Hydroxymethyl-(1,1’-biphenyl)-2-yl]-1-triphenylmethyltetrazole
• 4-Cloromethyl-5-methyl-1,3-dioxol-2-one
• Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate
• 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
• 4-(1-Methoxy-1-methylethyl)-2-propyl-1H-Imidazole-5-carboxylic acid ethyl ester
• Diethyl 2-propylImidazoledicarbonate