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
• Article Data: 4

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

General Description

The chemical "1-Cyclohexene-1-carboxylic acid, 4-[(1,1-dimethylethyl)amino]-5-(di-2-propenylamino)-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)-" is a complex organic compound with a cyclohexene carboxylic acid core, as well as a tert-butylamine, di-2-propenylamino, and 1-ethylpropoxy side chains. The compound also contains an ethyl ester group, and is in the (3R,4R,5S) stereochemical configuration. This chemical is likely to have various applications in the pharmaceutical and chemical industries, given its intricate structure and potential for interactions with biological systems.

Upstream product

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

Downstream Products

• 204255-11-8 oseltamivir phosphate 
• 196618-13-0 oseltamivir 
• 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.

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%.