1003888-24-1

Basic information

• Product Name: (S)-[2,2-dimethyl-1-(4-pyridin-2-yl-benzylidene-hydrazinocarbonyl)-propyl]-carbamic acid methyl ester
• Synonyms: (S)-[2,2-dimethyl-1-(4-pyridin-2-yl-benzylidene-hydrazinocarbonyl)-propyl]-carbamic acid methyl ester
• CAS NO: 1003888-24-1
• Molecular Weight: 368.436
• Mol File: 1003888-24-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-[2,2-dimethyl-1-(4-pyridin-2-yl-benzylidene-hydrazinocarbonyl)-propyl]-carbamic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-[2,2-dimethyl-1-(4-pyridin-2-yl-benzylidene-hydrazinocarbonyl)-propyl]-carbamic acid methyl ester(1003888-24-1)
• EPA Substance Registry System: (S)-[2,2-dimethyl-1-(4-pyridin-2-yl-benzylidene-hydrazinocarbonyl)-propyl]-carbamic acid methyl ester(1003888-24-1)

Safety Data

• Hazardous Substances Data: 1003888-24-1(Hazardous Substances Data)

Upstream product

• 24856-58-4 1,1-dimethoxy-1-(4-bromophenyl)methane 
• 162537-11-3 (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid 
• 20859-02-3 L-tert-Leucine 
• 198904-77-7 (S)-N'-(2-methoxycarbonylamino-3,3-dimethyl-butyryl)-hydrazinecarboxylic acid tert-butyl ester 
• 127406-56-8 4-(2'-pyridyl)benzaldehyde 
• 857904-00-8 (S)-(1-hydrazinocarbonyl-2,2-dimethyl-propyl)-carbamic acid methyl ester hydrochloride 
• 257907-05-4 N-[4-(2-pyridyl)phenylmethylidene]hydrazine 
• 198904-78-8 methyl (S)-(1-hydrazinyl-3,3-dimethyl-1-oxobutan-2-yl)carbamate 

Downstream Products

• 857904-02-0 {(S)-2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester 
• 1292296-09-3 1-[4-(pyridin-2-yl)phenyl]-2,5-bis{[N-(methoxycarbonyl)-L-tert-leucinyl]amino}-4(S)-hydroxy-6-phenyl-2-azahexane 
• 198904-31-3 atazanavir 
• 857900-54-0 {(S)-1-[N'-((2S,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester 

Relevant articles and documents

An efficient and practical synthesis of the HIV protease inhibitor atazanavir via a highly diastereoselective reduction approach

An efficient and practical synthesis of the HIV-1 protease inhibitor Atazanavir was developed by employing the diastereoselective reduction of ketomethylene aza-dipeptide isostere 10 as the key and final step. The high diastereoselectivity of the amino ketone reduction by lithium tri-iert-butoxyaluminum hydride in diethyl ether to afford the desired svn-1,2-amino alcohol structure was achieved by Felkin- Anh control as a result of the bulky and chiral N-(methoxycarbonyl)-L-tert-leucinyl moiety as the nitrogen protecting group. The coupling of the two key intermediates, N-(methoxycarbonyl)-L-tert-leucine acylated benzyl hydrazine 7 and chloromethyl ketone 9, via an SN2 reaction furnished the amino ketone 10 in high yield under our optimized conditions. Our new methodology features the late introduction of the S-hydroxyl group and the early acylation of benzyl hydrazine and chloromethyl ketone with N-(methoxycarbonyl)-L-tert-leucine, respectively, which confers high efficiency and easy purification.

PROCESS FOR SYNTHESIZING ATAZANAVIR

This invention relates to a process for synthesizing Atazanavir, Formula (I), including novel intermediates and novel steps to various intermediates along the synthetic pathway.

ANTIVIRAL PROTEASE INHIBITORS

The invention is related to compounds of Formula I or a pharmaceutically acceptable salt, solvate, ester, and /or phosphonate thereof, compositions containing such compounds, and therapeutic methods that include the administration of such compounds.