Aliskiren InterMediates

Base Information

• Chemical Name: Aliskiren InterMediates
• CAS No.: 393108-57-1
• Molecular Formula: C25H39BrO5
• Molecular Weight: 499.48
• Mol file: 393108-57-1.mol

Synonyms:

Chemical Property of Aliskiren InterMediates

Chemical Property:

• Density: 1.175

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Aliskiren InterMediates

There total 43 articles about Aliskiren InterMediates 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: 72.0%

C27H45NO4 → (3S,5S)-5-{(1R,3S)-1-bromo-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-dihydro-3-(1-methylethyl)furan-2(3H)-one (393108-57-1)

Guidance literature:

With N-Bromosuccinimide; phosphoric acid; In tetrahydrofuran; water; at 0 ℃; for 1.5h; H₃PO₄ and Br-compound were added alternatively;

Reference yield: 60.0%

(2S,7R,E)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-N,N,8-trimethylnon-4-enamide (325154-26-5) → (3S)-5-((3S)-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-1-bromo-4-methylpentyl)-3-isopropyl-dihydrofuran-2(3H)-one (1227379-42-1,393108-57-1)

Guidance literature:

With N-Bromosuccinimide; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; water; ethyl acetate;

Reference yield: 57.0%

(1S,3S)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methyl-1-[(2S,4S)-tetrahydro-4-isopropyl-5-oxo-furan-2-yl]pentyl methanesulfonate → (3S,5S)-5-{(1R,3S)-1-bromo-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-dihydro-3-(1-methylethyl)furan-2(3H)-one (393108-57-1)

Guidance literature:

(1S,3S)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methyl-1-[(2S,4S)-tetrahydro-4-isopropyl-5-oxo-furan-2-yl]pentyl methanesulfonate; With lithium bromide; In tetrahydrofuran; for 23h; Reflux;

With water; In tetrahydrofuran; stereoselective reaction;

DOI:10.1002/hlca.201200425

upstream raw materials:

(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol

(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

trans-(2S)-5-chloro-2-isopropyl-N,N-dimethyl-4-pentenamide

3-methylbutyric acid

Downstream raw materials:

(2S,4S,5R,7S)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methyl-2-isopropylnonanamide

Refernces

• 1、 Nam, Gyeok,Ko, Soo Y.. "A total synthesis of aliskiren". . p. 1937 - 1945,9. Retrieved 2012/12/12.
• 2、 -. "PROCESS FOR THE PREPARATION OF (2S,4S,5S,7S)-N-(2-CARBAMYL-2- METHYLPROPYL)-5-AMINO-4-HYDROXY-2,7-DIISOPROPYL-8-[4-METHOXY-3-(3- METHOXYPROPOXY)PHENYL]-OCTANAMIDE HEMIFUMARATE AND ITS INTERMEDIATES THEREOF". . . Retrieved 2011/12/14.