193140-43-1

Basic information

• Product Name: Glycine, N-(1-iminopentyl)- (9CI)
• Synonyms: Glycine, N-(1-iminopentyl)- (9CI);N-(1-Iminopentyl)-Glycine
• CAS NO: 193140-43-1
• Molecular Formula: C₇H₁₄N₂O₂
• Molecular Weight: 158.19826
• Product Categories: GLYCINESCAFFOLD
• Mol File: 193140-43-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 268.4±42.0 °C(Predicted)
• Appearance: /
• Density: 1.12±0.1 g/cm3(Predicted)
• PKA: 3.48±0.10(Predicted)
• CAS DataBase Reference: Glycine, N-(1-iminopentyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Glycine, N-(1-iminopentyl)- (9CI)(193140-43-1)
• EPA Substance Registry System: Glycine, N-(1-iminopentyl)- (9CI)(193140-43-1)

Safety Data

• Hazardous Substances Data: 193140-43-1(Hazardous Substances Data)

Usage

Uses

N-(1-Iminopentyl)glycine is used as a reactant in the preparation of (butyl)chloroimidazolecarboxaldehyde (losartan intermediate).

Upstream product

• 39739-46-3 methyl pentanimidate hydrochloride 
• 56-40-6 glycine 
• 110-59-8 pentanonitrile 
• 57246-71-6 methyl pentanimidate 

Downstream Products

• 114772-55-3 2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole 
• 124750-67-0 2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)methyl]imidazole-5-carboxaldehyde 
• 114798-26-4 lorsartan 
• 83857-96-9 2-n-butyl-5-Chloroimidazole-4-Carbaldehyde 
• 83857-96-9 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde 

Relevant articles and documents

A rapid and efficient synthesis of 2-butyl-5-chloro-3H-imidazole-4- carboxaldehyde

A rapid, efficient, cost effective procedure has been developed for the synthesis of 2-butyl-5-chloro-3H-imidazole-4-carboxaldehyde. Preparation of methyl pentanimidate was accomplished in just 12 hours, followed by a sequence of reactions without isolation and purification of the formed intermediates. The final compound was purified by simple acid-base treatment to get a product with 99.9% HPLC purity.

An efficient and green synthetic route to losartan

A practical, efficient and green process for the preparation of losartan, an antihypertensive drug, has been developed with an overall yield of 58.6%. The key step is the synthesis of the two key intermediates 2-butyl-4-chloro-3H-imidazole-5-carbaldehyde (BCFI) and 2-cyano-4'-methyl biphenyl (OTBN). BCFI was synthesised from valeronitrile and acetyl chloride by three steps with an overall yield of 69%; OTBN was obtained in 86% yield by the coupling of o-chlorobenzonitrile with p-methylphenylmagnesium chloride in tetrahydrofuran in the presence of manganese chloride and chlorotrimethylsilane. The above route was successfully operated in at a pilot-plant operation.

Novel Syntheses of 2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde: A Key Intermediate for the Synthesis of the Angiotensin II Antagonist Losartan

Reaction of glycine methyl ester (19) with imidate 18 under carefully optimized conditions allowed preparation of the rather unstable imidazolinone 11 in ca. 90% yield. Reaction of 11 with POCl3/ DMF followed by aqueous workup gave aldehyde 2, a key intermediate for the synthesis of the angiotensin II antagonist Losartan, in ca. 55% yield. Structural identification of intermediates and byproducts formed during both the reaction to prepare 11 and the reaction of 11 with POCl3/DMF allowed development of several closely related syntheses of aldehyde 2.