1292296-09-3

Basic information

• Product Name: (3S,8R,9S,12S)-3,12-Bis(1,1-diMethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylMethyl)-6-[[4-(2-pyridinyl)phenyl]Methyl]-,2,5,6,10,13-pentaazatetradecanedioic Acid 1,14-DiMethyl Ester
• Synonyms: (3S,8R,9S,12S)-3,12-Bis(1,1-diMethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylMethyl)-6-[[4-(2-pyridinyl)phenyl]Methyl]-,2,5,6,10,13-pentaazatetradecanedioic Acid 1,14-DiMethyl Ester;8-epi Atazanavir;Atazanavir IMpurity 1;Atazanavir S,R,S,S-diastereomer
• CAS NO: 1292296-09-3
• Molecular Formula: C38H54N6O7
• Molecular Weight: 706.87136
• Product Categories: Chiral Reagents;Impurities;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1292296-09-3.mol
• Article Data: 20

Chemical Properties

• Appearance: /
• Density: 1.178±0.06 g/cm3(Predicted)
• PKA: 11.11±0.46(Predicted)
• CAS DataBase Reference: (3S,8R,9S,12S)-3,12-Bis(1,1-diMethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylMethyl)-6-[[4-(2-pyridinyl)phenyl]Methyl]-,2,5,6,10,13-pentaazatetradecanedioic Acid 1,14-DiMethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,8R,9S,12S)-3,12-Bis(1,1-diMethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylMethyl)-6-[[4-(2-pyridinyl)phenyl]Methyl]-,2,5,6,10,13-pentaazatetradecanedioic Acid 1,14-DiMethyl Ester(1292296-09-3)
• EPA Substance Registry System: (3S,8R,9S,12S)-3,12-Bis(1,1-diMethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylMethyl)-6-[[4-(2-pyridinyl)phenyl]Methyl]-,2,5,6,10,13-pentaazatetradecanedioic Acid 1,14-DiMethyl Ester(1292296-09-3)

Safety Data

• Hazardous Substances Data: 1292296-09-3(Hazardous Substances Data)

Usage

Uses

An epimeric impurity of Atazanavir, novel azapeptide HIV protease inhibitor.

Upstream product

• 149451-80-9 (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol 
• 437713-03-6 methanesulfonic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenyl-propyl ester 
• 87199-17-5 4-formylphenylboronic acid, 
• 198904-84-6 2-[4-(2-pyridinyl)phenyl]methylenehydrazinecarboxylic acid tert-butyl ester 
• 920757-34-2 1-(4-(pyridin-2-yl)benzyl)hydrazine 
• 162537-11-3 (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid 
• 198904-87-9 1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride 
• 102123-74-0 (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 
• 127406-56-8 4-(2'-pyridyl)benzaldehyde 
• 24856-58-4 1,1-dimethoxy-1-(4-bromophenyl)methane 
• 20859-02-3 L-tert-Leucine 
• 52735-71-4 L-phenylalanine chloromethyl ketone 
• 1003888-24-1 (S)-[2,2-dimethyl-1-(4-pyridin-2-yl-benzylidene-hydrazinocarbonyl)-propyl]-carbamic acid methyl ester 
• 1033125-49-3 2-(4-dimethoxymethylphenyl)pyridine 

Relevant articles and documents

A facile and efficient synthesis of d3-labelled Reyataz

A facile and efficient synthesis of d3-labelled Reyataz is described. The key step of synthesis involved the coupling of N-(d 3-methoxycarbonyl)-L-tert-leucine 2b with an advanced chiral non-racemic building block 4. The latter was synthesized in 4 steps from the readily accessible hydrazine derivative 8. Copyright

Method for synthesis of atazanavir

The invention discloses a method for synthesis of atazanavir. The method comprises that a compound methyl (S)-1-((S)-2-ethoxyethyl-1-phenylethane-2-yl-amino)-3, 3-dimethyl-1-carbonylbutane-2-yl-carbamate shown in the formula V and a compound N-1-[N-(methoxycarbonyl)-L-tertiary leucine]-N-2-[4-(2-pyridyl)-benzyl]hydrazine shown in the formula VIII undergo a nucleophilic substitution reaction in anorganic solvent to produce a compound 1-[4-(2-pyridyl)phenyl]-5(S)-2, 5-bis{[N-(methoxycarbonyl)-L-tertiary leucine]amino}-4(S)-hydroxy-6-phenyl-2-azahexane VIII shown in the formula IX, wherein the compound shown in the formula IX is atazanavir. The method utilizes raw materials having a wide raw material source, the product is easy to purify, a cost is low, the synthesis processes are simple, the operation is simple, the process is simple, special requirement on equipment is avoided and large-scale production feasibility is realized.

A process for preparing Atazanavir monomer

The invention discloses a method for preparing an atazanavir monomer. The method is applied to the technical field of medicines and comprises steps as follows: at the proper temperature, weak base is used as an acid-binding agent, under a certain organic solvent condition, N-methoxycarbonyl-L-tert-leucine firstly reacts with thionyl chloride to produce N-methoxycarbonyl-L-tert-leucine acyl chloride, then the N-methoxycarbonyl-L-tert-leucine acyl chloride and 1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxyl-5(S)-2,5-diamino-6-phenyl-2-azahexane have an amide formation reaction at the room temperature, and the atazanavir monomer is obtained. The method has the advantages as follows: (1), the thionyl chloride is cheap, so that the costs of raw materials are effectively reduced, and the method is suitable for industrialization; (2), the produced pollution is less and is converted into soluble effluent brine after after-treatment, so that the method is relatively environment-friendly; (3), the operation is simple, the product yield is high, separation and purification are easy, and the method is suitable for industrial production.