651324-06-0

Basic information

• Product Name: 1-Cyclohexene-1-carboxylic acid, 4-[(1,1-dimethylethyl)amino]-5-(di-2-propenylamino)-3-(1-ethylpropoxy)- , ethyl ester, (3R,4R,5S)-
• CAS NO: 651324-06-0
• Molecular Formula: C24H42N2O3
• Molecular Weight: 406.609
• Mol File: 651324-06-0.mol

Chemical Properties

• Boiling Point: 479.9±45.0 °C(Predicted)
• Density: 0.98±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1-Cyclohexene-1-carboxylic acid, 4-[(1,1-dimethylethyl)amino]-5-(di-2-propenylamino)-3-(1-ethylpropoxy)- , ethyl ester, (3R,4R,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexene-1-carboxylic acid, 4-[(1,1-dimethylethyl)amino]-5-(di-2-propenylamino)-3-(1-ethylpropoxy)- , ethyl ester, (3R,4R,5S)-(651324-06-0)
• EPA Substance Registry System: 1-Cyclohexene-1-carboxylic acid, 4-[(1,1-dimethylethyl)amino]-5-(di-2-propenylamino)-3-(1-ethylpropoxy)- , ethyl ester, (3R,4R,5S)-(651324-06-0)

Safety Data

• Hazardous Substances Data: 651324-06-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Cyclohexene-1-carboxylic acid, 4-[(1,1-dimethylethyl)amino]-5-(di-2-propenylamino)-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)is used as a pharmaceutical compound for its potential to interact with biological systems. 1-Cyclohexene-1-carboxylic acid,
4-[(1,1-dimethylethyl)amino]-5-(di-2-propenylamino)-3-(1-ethylpropoxy)-
, ethyl ester, (3R,4R,5S)-'s unique structure and functional groups may allow it to target specific receptors or enzymes, making it a candidate for the development of new drugs.
Used in Chemical Industry:
In the chemical industry, 1-Cyclohexene-1-carboxylic acid, 4-[(1,1-dimethylethyl)amino]-5-(di-2-propenylamino)-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)may be utilized as a building block or intermediate in the synthesis of other complex organic molecules. Its versatile structure and functional groups can be further modified or incorporated into larger molecules for various applications, such as in the production of specialty chemicals, materials, or agrochemicals.

Upstream product

• 124-02-7 diallylamine 
• 204254-96-6 (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester 
• 651324-04-8 (3R,4S,5R)-[5-(tert-butylamino)-4-hydroxy-3-(pent-3-yloxy)]cyclohex-1-ene-1-carboxylic acid ethyl ester 
• 651324-05-9 ethyl (3R,4S,5R)-4,5-(1,1-Dimethylethyl)imino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate 

Downstream Products

• 196618-13-0 oseltamivir 
• 204255-11-8 oseltamivir phosphate 
• 651324-07-1 ethyl (3R,4R,5S)-4-N-acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate 

Relevant articles and documents

Method for preparing antiviral drug oseltamivir phosphate intermediate tert-butylamine derivative I

The invention discloses a method for preparing a tert-butylamine derivative, and relates to the field of drug synthesis. The method comprises the following steps: 1, preparing a magnesium-amine compound, namely, adding magnesium halide and tert-butylamine A into an aprotic solvent, and carrying out a mixing stirring reaction for 0.5-1.5 h at a temperature of 0-15 DEG C to prepare a mixed solutionA; 2, adding a compound B into the mixed solution A prepared in the step 1, and carrying out a stirring reaction for more than 8 hours to prepare a mixed solution B; and 3, supplementing tert-butylamine D into the mixed solution B prepared in the step 2, and carrying out a stirring reaction for 24-48h at a temperature of 50-70 DEG C to prepare a tert-butylamine derivative I. By controlling the preparation temperature of the compound, the addition mode of tert-butylamine and the time of the ring-opening reaction, the curing phenomenon in the reaction and the increase of by-products can be effectively controlled.

Process for preparing 1,2-diamino compounds

The invention provides a multi-step process for preparing 1,2-diamino compounds of formula wherein R1, R1′, R2, R2′, R3 and R4 have the meaning given in the specification and pharmaceutically acceptable addition salts thereof, from 1,2-epoxides of formula wherein R1, R1′, R2 and R2′ have the meaning given in the specification.

The synthetic development of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu): A challenge for synthesis & process research

The evolution of the synthesis of oseltamivir phosphate (Tamiflu), used for the oral treatment and prevention of influenza virus infections (viral flu) is described. Oseltamivir phosphate is the ethyl ester prodrug of the corresponding acid, a potent and selective inhibitor of influenza neuraminidase. The discovery chemistry route and scalable routes used for kilo laboratory production as well as the technical access to oseltamivir phosphate from (-)-shikimic acid proceeding via a synthetically well-developed epoxide building block followed by azide transformations are reviewed. Synthesis and process research investigations towards azide-free conversions of the key epoxide building block to oseltamivir phosphate are discussed. The search for new routes to oseltamivir phosphate independent of shikimic acid including Diels-Alder approaches and transformations of aromatic rings employing a desymmetrization concept are presented in view of large-scale production requirements.

Research and Development of a Second-Generation Process for Oseltamivir Phosphate, Prodrug for a Neuraminidase Inhibitor

A second-generation manufacturing process from a shikimic acid-derived epoxide to oseltamivir phosphate features a magnesium chloride - amine complex-catalyzed ring opening of the epoxide by tert-butylamine, a selective O-sulfonylation of the resulting tert-butylamino alcohol, a surprisingly efficient cleavage of a tert-butyl group from an aliphatic tert-butylamide, and the isolation of oseltamivir phosphate from a palladium-catalyzed allyl transfer reaction mixture. The overall yield from the epoxide to oseltamivir phosphate has been increased from 27 to 29% or 35-38% for two previous processes, respectively, to 61%.