12-Oxa-2,5,6,10-tetraazatetradecanoic acid, 3-(1,1-diMethylethyl)-8-hydroxy-13,13-diMethyl-4,11-dioxo-9-(phenylMethyl)-6-[[4-(2-pyridinyl)phenyl]Methyl]-, Methyl ester, (3S,8S,9S)-

Base Information

• Chemical Name: 12-Oxa-2,5,6,10-tetraazatetradecanoic acid, 3-(1,1-diMethylethyl)-8-hydroxy-13,13-diMethyl-4,11-dioxo-9-(phenylMethyl)-6-[[4-(2-pyridinyl)phenyl]Methyl]-, Methyl ester, (3S,8S,9S)-
• CAS No.: 857904-03-1
• Molecular Formula: C35H47N5O6
• Molecular Weight: 633.788
• Mol file: 857904-03-1.mol

Synonyms:Tert-butyl (1S,2S)-1-benzyl-2-hydroxy-3-{2-{(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}-1-[4-(2-pyridinyl)benzyl]hydrazino}propylcarbamate;methyl (S)-1-(2-((2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutyl)-2-(4-(pyridin-2-yl)benzyl)hydrazinyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate;

Chemical Property of 12-Oxa-2,5,6,10-tetraazatetradecanoic acid, 3-(1,1-diMethylethyl)-8-hydroxy-13,13-diMethyl-4,11-dioxo-9-(phenylMethyl)-6-[[4-(2-pyridinyl)phenyl]Methyl]-, Methyl ester, (3S,8S,9S)-

Chemical Property:

• PSA: 142.12000
• LogP: 6.02210

Purity/Quality:

Methy(3S,8S,9S)-3-(1,1-Dimethylethyl)-8-hydroxy-13,13-dimethyl-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-12-oxa-2,5,6,10-tetraazatetradecanoicAcidEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methy (3S,8S,9S)-3-(1,1-Dimethylethyl)-8-hydroxy-13,13-dimethyl-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-12-oxa-2,5,6,10-tetraazatetradecanoic Acid Ester is an intermediate used in the synthesis of Atazanavir-d9 (A790053), which is the deuterated analog of Atazanavir (A790051), a azapeptide HIV protease inhibitor derivative. Atazanavir have been investigated as potential treatment of human immunodeficiency virus (HIV) and for anticancer purposes.

Technology Process of 12-Oxa-2,5,6,10-tetraazatetradecanoic acid, 3-(1,1-diMethylethyl)-8-hydroxy-13,13-diMethyl-4,11-dioxo-9-(phenylMethyl)-6-[[4-(2-pyridinyl)phenyl]Methyl]-, Methyl ester, (3S,8S,9S)-

There total 9 articles about 12-Oxa-2,5,6,10-tetraazatetradecanoic acid, 3-(1,1-diMethylethyl)-8-hydroxy-13,13-diMethyl-4,11-dioxo-9-(phenylMethyl)-6-[[4-(2-pyridinyl)phenyl]Methyl]-, Methyl ester, (3S,8S,9S)- 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: 65.0%

{(S)-2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester (857904-02-0) + (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2) → {(1S,2S)-1-benzyl-2-hydroxy-3-[N'-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyryl)-N-(4-pyridin-2-yl-benzyl)-hydrazino]-propyl}-carbamic acid tert-butyl ester (857904-03-1)

Guidance literature:

In hexane; isopropyl alcohol; at 65 ℃; for 60h;

Reference yield: 30.8%

{(S)-2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester (857904-02-0) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → {(1S,2S)-1-benzyl-2-hydroxy-3-[N'-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyryl)-N-(4-pyridin-2-yl-benzyl)-hydrazino]-propyl}-carbamic acid tert-butyl ester (857904-03-1)

Guidance literature:

In isopropyl alcohol; for 16h; Reflux;

Reference yield:

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid (162537-11-3) → {(1S,2S)-1-benzyl-2-hydroxy-3-[N'-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyryl)-N-(4-pyridin-2-yl-benzyl)-hydrazino]-propyl}-carbamic acid tert-butyl ester (857904-03-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 14.43 g / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; ethyldiisopropylamine / CH₂Cl₂ / 1.5 h / 20 °C

2: 25 percent / propan-2-ol / 24 h / Heating

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

DOI:10.1002/jlcr.1019

upstream raw materials:

{(S)-2,2-dimethyl-1-[N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-propyl}-carbamic acid methyl ester

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

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

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

Downstream raw materials:

methyl (1R,3S)-3-((2S,3S)-3-hydroxy-4-(2-((S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl)-1-(4-(pyridin-2-yl)benzyl)hydrazinyl)-1-phenylbutan-2-ylcarbamoyl)-2,2-dimethylcyclobutylcarbamate

methyl (S)-1-(2-((2S,3S)-3-((1S,3R)-3-(tert-butoxycarbonylamino)-2,2-dimethylcyclobutanecarboxamido)-2-hydroxy-4-phenylbutyl)-2-(4-(pyridin-2-yl)benzyl)hydrazinyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

methyl (S)-1-(2-((2S,3S)-3-((1S,3R)-3-acetamido-2,2-dimethylcyclobutanecarboxamido)-2-hydroxy-4-phenylbutyl)-2-(4-(pyridin-2-yl)benzyl)hydrazinyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

methyl (S)-1-(2-((2S,3S)-2-hydroxy-3-((1R,3S)-3-(methoxycarbonylamino)-2,2-dimethylcyclobutanecarboxamido)-4-phenylbutyl)-2-(4-(pyridin-2-yl)benzyl)hydrazinyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

Refernces

• 1、 -. "ANTIVIRAL PROTEASE INHIBITORS". Page/Page column 454; 511. . Retrieved 2008/06/13.
• 2、 -. "HIV PROTEASE INHIBITING COMPOUNDS". Page/Page column 110. . Retrieved 2010/02/12.