651324-04-8

Basic information

• Product Name: 1-Cyclohexene-1-carboxylic acid, 5-[(1,1-dimethylethyl)amino]-3-(1-ethylpropoxy)-4-hydroxy-, ethyl ester, (3R,4S,5R)-
• Synonyms: ethyl (3R,4S,5R)-5-N-(1,1-dimethylethyl)amino-3-(1-ethylpropoxy)-4-hydroxy-cyclohexene-1-carboxylate
• CAS NO: 651324-04-8
• Molecular Formula: C18H33NO4
• Molecular Weight: 327.464
• Mol File: 651324-04-8.mol

Chemical Properties

• Boiling Point: 425.7±45.0 °C(Predicted)
• Density: 1.03±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1-Cyclohexene-1-carboxylic acid, 5-[(1,1-dimethylethyl)amino]-3-(1-ethylpropoxy)-4-hydroxy-, ethyl ester, (3R,4S,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexene-1-carboxylic acid, 5-[(1,1-dimethylethyl)amino]-3-(1-ethylpropoxy)-4-hydroxy-, ethyl ester, (3R,4S,5R)-(651324-04-8)
• EPA Substance Registry System: 1-Cyclohexene-1-carboxylic acid, 5-[(1,1-dimethylethyl)amino]-3-(1-ethylpropoxy)-4-hydroxy-, ethyl ester, (3R,4S,5R)-(651324-04-8)

Safety Data

• Hazardous Substances Data: 651324-04-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
1-Cyclohexene-1-carboxylic acid, 5-[(1,1-dimethylethyl)amino]-3-(1-ethylpropoxy)-4-hydroxy-, ethyl ester, (3R,4S,5R)is used as a pharmaceutical agent or starting material for the synthesis of related compounds with biological activity in the pharmaceutical industry. Its specific stereochemistry and unique chemical structure contribute to its potential as a drug candidate, making it valuable for research and development purposes.

Upstream product

• 75-64-9 tert-butylamine 
• 204254-96-6 (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester 
• 757965-01-8 (1S,5R,6R)-5-(1-ethyl-propoxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester 

Downstream Products

• 651324-06-0 ethyl (3R,4R,5S)-5-N,N-diallylamino-4-(1,1-dimethylethyl)amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate 
• 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 
• 196618-13-0 oseltamivir 
• 204255-11-8 oseltamivir phosphate 

Relevant articles and documents

Preparation method of oseltamivir phosphate key intermediate hydrochloride

The invention relates to the technical field of drug synthesis, and particularly discloses a preparation method of oseltamivir phosphate key intermediate hydrochloride, which comprises the following steps: reacting tert-butylamine with epoxide under the condition of taking anhydrous magnesium chloride as a catalyst to generate an intermediate product A; adding methanesulfonyl chloride and triethylamine to generate an intermediate product B; adding diallylamine and benzenesulfonic acid to generate an intermediate product C, and adding acetic anhydride and anhydrous sodium acetate to generate an intermediate product D; and preparing an intermediate product D ethanol solution, dropwise adding the intermediate product D ethanol solution into a saturated hydrogen chloride ethanol solution, conducting stirring, conducting standing, carrying out suction filtration, conducting washing, conducting pulping, carrying out suction filtration, and conducting drying. According to the preparation method disclosed by the invention, oseltamivir phosphate key intermediate hydrochloride is successfully separated and obtained, and the yield is relatively high.

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%.

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.