651324-07-1

Basic information

• Product Name: ethyl (3R,4R,5S)-4-N-acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
• Synonyms: ethyl (3R,4R,5S)-4-N-acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
• CAS NO: 651324-07-1
• Molecular Weight: 448.646
• Mol File: 651324-07-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: ethyl (3R,4R,5S)-4-N-acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (3R,4R,5S)-4-N-acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate(651324-07-1)
• EPA Substance Registry System: ethyl (3R,4R,5S)-4-N-acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate(651324-07-1)

Safety Data

• Hazardous Substances Data: 651324-07-1(Hazardous Substances Data)

Usage

Uses

Ethyl (3R,4R,5S)-4-N-Acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate is an intermediate in the synthesis of Oseltamivir Phosphate (O701000), a prodrug for Oseltamivir (O701005).

Upstream product

• 757965-01-8 (1S,5R,6R)-5-(1-ethyl-propoxy)-7-oxa-bicyclo[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 
• 204254-96-6 (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester 
• 124-02-7 diallylamine 
• 108-24-7 acetic anhydride 
• 651324-06-0 ethyl (3R,4R,5S)-5-N,N-diallylamino-4-(1,1-dimethylethyl)amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate 

Downstream Products

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

Relevant articles and documents

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.