312904-15-7

Basic information

• Product Name: 1-Cyclohexene-1-carboxylic acid, 4-amino-3-(1-ethylpropoxy)-5-(2-propenylamino)-, ethyl ester, (3R,4R,5S)-
• CAS NO: 312904-15-7
• Molecular Formula: C17H30N2O3
• Molecular Weight: 310.437
• Mol File: 312904-15-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-Cyclohexene-1-carboxylic acid, 4-amino-3-(1-ethylpropoxy)-5-(2-propenylamino)-, ethyl ester, (3R,4R,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexene-1-carboxylic acid, 4-amino-3-(1-ethylpropoxy)-5-(2-propenylamino)-, ethyl ester, (3R,4R,5S)-(312904-15-7)
• EPA Substance Registry System: 1-Cyclohexene-1-carboxylic acid, 4-amino-3-(1-ethylpropoxy)-5-(2-propenylamino)-, ethyl ester, (3R,4R,5S)-(312904-15-7)

Safety Data

• Hazardous Substances Data: 312904-15-7(Hazardous Substances Data)

Upstream product

• 144-55-8 sodium hydrogencarbonate 
• 107-11-9 1-amino-2-propene 
• 124-63-0 methanesulfonyl chloride 
• 877238-97-6 ethyl (3R,4S,5R)-3-(1-ethylpropoxy)-5-N-formylamino-4-methanesulfonyloxy-1-cyclohexene-1-carboxylate 
• 332047-22-0 ethyl (3R,4S,5R)-5-N-formylamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate 
• 332047-17-3 ethyl (3R,4S,5R)-5-N-benzylideneamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate 
• 312904-11-3 ethyl (3R,4S,5R)-5-N-allyllamino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate 
• 312904-12-4 ethyl (3R,4S,5R)-5-amino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate 
• 204254-96-6 (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester 
• 332047-18-4 ethyl (3R,4S,5R)-5-N-benzylideneamino-3-(1-ethylpropoxy)-4-methanesulfonyloxy-1-cyclohexene-1-carboxylate 

Downstream Products

• 196618-13-0 oseltamivir 
• 312904-18-0 ethyl (3R,4R,5S)-4-N-acetylamino-5-N-allylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate 

Relevant articles and documents

Process for the preparation of 4,5-diamino shikimic acid derivatives

The present invention relates to a process for the preparation of a 4,5-diamino shikimic acid derivative of formula and pharmaceutically acceptable addition salts thereof wherein R1, R1′ are independent of each other H or alkyl, R2 is an alkyl and R3, R4 are independent of each other H or an alkanoyl, with the proviso that not both R3 and R4 are H. 4,5-diamino shikimic acid derivatives of formula I, especially the (3R,4R,5S)-5-amino-4-acetylamino-3-(1-ethyl-propoxy)-cyclohex-1-ene-carboxylic acid ethyl ester and its pharmaceutically acceptable additional salts are potent inhibitors of viral neuraminidase.

Process for preparing 1,2-diamino compounds

The invention provides a multistep process for preparing 1,2-diamino compounds and pharmaceutically acceptable addition salts thereof from 1,2-epoxides.

New, azide-free transformation of epoxides into 1,2-diamino compounds: Synthesis of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu)

A new, azide-free transformation of the key precursor epoxide 6 to the influenza neuraminidase inhibitor prodrug oseltamivir phosphate (1, Tamiflu) is described. This sequence represents a new and efficient transformation of an epoxide into a 1,2-diamino compound devoid of potentially toxic and hazardous azide reagents and intermediates and avoids reduction and hydrogenation conditions. Using catalytic MgBr2·OEt2 as a new, inexpensive Lewis acid, the introduction of the first amino function was accomplished by opening of the oxirane ring with allylamine followed by Pd/C-catalyzed deallylation to the amino alcohol 16. The introduction of the second amino group was then accomplished via an efficient reaction cascade involving a domino sequence preferably utilizing a transient imino protection. Selective acetylation of the resulting diamine 17 was achieved under acidic conditions providing the crystalline 4-acetamido-5-N-allylamino-derivative 18, which upon deallylation over Pd/C and phosphate salt formation afforded drug substance 1. The overall yield of this route from 6 of 35-38% exceeds the yield of the azide-based process (27-29%) and does not require any chromatographic purification.