112243-70-6

Basic information

• Product Name: ethyl N-[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]-L-norvalinate
• Synonyms: Ethyl N-[(2S)-1-(benzyloxy)-1-oxopropan-2-yl]-L-norvalinate
• CAS NO: 112243-70-6
• Molecular Formula: C₁₇H₂₅NO₄
• Molecular Weight: 307.3847
• EINECS: 601-174-6
• Mol File: 112243-70-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 400.791°C at 760 mmHg
• Flash Point: 196.191°C
• Density: 1.07g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: Refrigerator
• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• CAS DataBase Reference: ethyl N-[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]-L-norvalinate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl N-[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]-L-norvalinate(112243-70-6)
• EPA Substance Registry System: ethyl N-[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]-L-norvalinate(112243-70-6)

Safety Data

• Hazardous Substances Data: 112243-70-6(Hazardous Substances Data)

Usage

Description

Ethyl N-[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]-L-norvalinate is a complex organic compound with a specific stereochemistry and functional groups. It is characterized by its molecular structure, which includes a benzyloxy group, a methyl group, and an ester functional group. ethyl N-[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]-L-norvalinate is likely to have specific applications in the pharmaceutical or chemical industries due to its unique structural features.

Uses

Used in Pharmaceutical Industry:
Ethyl N-[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]-L-norvalinate is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the chemical industry, ethyl N-[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]-L-norvalinate can be used as a starting material or intermediate for the synthesis of other complex organic molecules. Its versatility in chemical reactions allows for the creation of a wide range of products with different applications.
For example, N-[(S)-1-Carbethoxybutyl]-(S)-alanine Benzyl Ester, which is an intermediate for the synthesis of N-[(R)-1-Carbethoxybutyl]-(S)-alanine (C178000), is used in the production of Perindoprilat (P287530), an angiotensin-converting enzyme (ACE) inhibitor. This demonstrates the importance of ethyl N-[(1S)-2-(benzyloxy)-1-methyl-2-oxoethyl]-L-norvalinate and similar compounds in the development of antihypertensive medications.

Upstream product

• 17831-01-5 H-Ala-OBzl 
• 109684-05-1 ethyl 2-([(trifluoromethyl)sulphonyl]oxy)pentanoate 
• 39256-85-4 ethyl 2-amino-L-butyrate 

Downstream Products

• 82834-12-6 N-<1(S)-(ethoxycarbonyl)butyl>-L-alanine 
• 109715-02-8 (R)-5-tert-Butyl-3-[(S)-2-((S)-1-ethoxycarbonyl-butylamino)-propionyl]-2,3-dihydro-[1,3,4]thiadiazole-2-carboxylic acid benzyl ester 
• 109785-12-8 (S)-5-tert-Butyl-3-[(S)-2-((S)-1-ethoxycarbonyl-butylamino)-propionyl]-2,3-dihydro-[1,3,4]thiadiazole-2-carboxylic acid benzyl ester 

Relevant articles and documents

NOVEL METHOD FOR PREPARATION OF CRYSTALLINE PERINDOPRIL ERBUMINE

A process for preparation of crystalline perindopril erbumine of formula (II) which exhibits the X-ray (powder) diffraction pattern like that shown in the figure. The process comprises reacting a solution of perindopril of formula (I), in a solvent selected from N, N-dimethylformamide or dimethyl acetals of lower aliphatic aldehydes and ketones with tertiary butylamine and crystallization of the erbumine salt thus obtained by heating the reaction mixture to reflux, filtering hot, cooling gradually to 20 oC to 30 oC, and further cooling to 0o C to 15 oC for 30 minutes to 1 hour and finally filtering off and drying the crystals.

Design, synthesis, and physicochemical properties of a novel, conformationally restricted 2,3-dihydro-1,3,4-thiadiazole-containing angiotensin converting enzyme inhibitor which is preferentially eliminated by the biliary route in rats

Two novel series of dihydrothiadiazole ring containing inhibitors of angiotensin converting enzyme have been designed and synthesized. The compounds are highly potent enzyme inhibitors and, as a consequence of conformational restriction, chemically stable with respect to undesirable cyclization reactions. The most interesting compound from this series, 5a (FPL 63547), is the monoethyl ester prodrug of the highly potent ''aminocarboxy'' inhibitor 5b (FPL 63674). It produces an antihypertensive effect of long duration in animal models after oral dosing. Unlike other ACE inhibitors, 5b is eliminated almost entirely by biliary clearance in the rat. The favorable pharmacological properties of 5a and 5b are rationalized in terms of their unique physicochemical profiles. The clear preference for biliary clearance seen with 5b is consistent with its lipophilicity and its high degree of net ionization at physiological pH, which results from the very low pK(a) of the C-terminus carboxylic acid function. FPL 63547 is presently undergoing clinical investigation in man.