(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

Base Information

• Chemical 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
• CAS No.: 1292296-09-3
• Molecular Formula: C₃₈H₅₂N₆O₇
• Molecular Weight: 704.867
• Mol file: 1292296-09-3.mol

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

Chemical Property of (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

Chemical Property:

• PKA: 11.11±0.46(Predicted)
• PSA: 185.18000
• Density: 1.178±0.06 g/cm3(Predicted)
• LogP: 6.30100

Purity/Quality:

98%,99%, ^*data from raw suppliers

8-epiAtazanavir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (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

There total 75 articles about (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 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C14H18N4O4 (869285-68-7) + 1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride (198904-87-9) → atazanavir (198904-31-3,1292296-09-3)

Guidance literature:

With dipotassium hydrogenphosphate; In water; at 5 - 40 ℃;

Reference yield: 95.0%

C14H18N4O4 (869285-68-7) + 1-[4-(Pyridin-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane.3hydrochloride → atazanavir (198904-31-3,1292296-09-3)

Guidance literature:

With dipotassium hydrogenphosphate; In water; at 5 - 40 ℃; for 1.5 - 2h;

Reference yield: 95.0%

{(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 (857900-54-0) + (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid (162537-11-3) → atazanavir (198904-31-3,1292296-09-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1002/jlcr.1019

upstream raw materials:

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride

{(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

1-(4-(pyridin-2-yl)benzyl)hydrazine

Refernces

• 1、 -. "TABLETED COMPOSITIONS CONTAINING ATAZANAVIR". . . Retrieved 2018/06/01.
• 2、 -. "Method for synthesizing atazanavir". Paragraph 0012; 0017. . Retrieved 2017/09/13.