Aliskiren inter-10

Base Information

• Chemical Name: Aliskiren inter-10
• CAS No.: 365541-74-8
• Molecular Formula: C23H27NO4
• Molecular Weight: 381.472
• Mol file: 365541-74-8.mol

Synonyms:(4R)-3-[(2S)-3-Methyl-1-oxo-2-[(phenylmethoxy)methyl]butyl]-4-(phenylmethyl)oxazolidin-2-one;

Chemical Property of Aliskiren inter-10

Chemical Property:

• Melting Point: 74-75 ºC
• Refractive Index: 1.566
• Boiling Point: 535.9 °C at 760 mmHg
• Flash Point: 277.9 °C
• PSA: 55.84000
• Density: 1.165 g/cm³
• LogP: 4.00340

Purity/Quality:

99% ^*data from raw suppliers

(4R)-3-[(2S)-3-METHYL-1-OXO-2-[(PHENYLMETHOXY)METHYL]BUTYL]-4-(PHENYLMETHYL)-2-OXAZOLIDINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Aliskiren inter-10

There total 7 articles about Aliskiren inter-10 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%

Benzyloxymethyl chloride (3587-60-8) + (R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one (145589-03-3) → (4R)-3-{(2S)-3-methyl-1-oxo-2-[(phenylmethoxy)methyl]butyl}-4-(phenylmethyl)oxazolidin-2-one (365541-74-8)

Guidance literature:

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.166667h;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;

Benzyloxymethyl chloride; In dichloromethane; for 16h;

Reference yield: 50.0%

Benzyloxymethyl chloride (3587-60-8) + (R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one (145589-03-3) → 4-(R)-benzyl-3-(2-(R)-benzyloxymethyl-3-methylbutyryl)oxazolidin-2-one (470454-06-9) + (4R)-3-{(2S)-3-methyl-1-oxo-2-[(phenylmethoxy)methyl]butyl}-4-(phenylmethyl)oxazolidin-2-one (365541-74-8)

Guidance literature:

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;

Benzyloxymethyl chloride; In dichloromethane; at 0 ℃; for 20h;

DOI:10.1002/hlca.200390235

Reference yield:

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) → (4R)-3-{(2S)-3-methyl-1-oxo-2-[(phenylmethoxy)methyl]butyl}-4-(phenylmethyl)oxazolidin-2-one (365541-74-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 100 percent / tetrahydrofuran; hexane / 4 h / -78 - 0 °C

2.1: TiCl₄ / CH₂Cl₂ / 0.17 h / 0 °C

2.2: i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

2.3: 95 percent / TiCl₄ / CH₂Cl₂ / 2 h / 0 °C

3.1: 89 percent / CF₃SO₃H / CH₂Cl₂; cyclohexane / 2 h / 25 °C

With n-butyllithium; trifluorormethanesulfonic acid; titanium tetrachloride; In tetrahydrofuran; hexane; dichloromethane; cyclohexane;

DOI:10.1021/ja011271s

upstream raw materials:

Benzyloxymethyl chloride

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one

benzyl alcohol

(R)-4-(phenylmethyl)-2-oxazolidinone

Downstream raw materials:

(2S,4S)-2-(tert-butoxycarbonyl)amino-4-(benzyloxymethyl)-5-methyl-hexanal

tert-butyl (3(S)-benzyloxymethyl-1(S)-hydroxymethyl-4-methyl-pentyl)carbamate

tert-butyl (1S,3S)-3-(benzyloxymethyl)-4-methyl-1-((R)-oxiran-2-yl)pentylcarbamate

tert-butyl (2S,3S,5S)-1-amino-5-(benzyloxymethyl)-2-hydroxy-6-methylheptan-3-ylcarbamate

Refernces

• 1、 -. "Quinolizinone compound and use thereof as HIV integrase inhibitor". Page/Page column 47. . Retrieved 2010/10/20.
• 2、 Goeschke, Richard,Stutz, Stefan,Heinzelmann, Walter,Maibaum, Juergen. "The nonchiral bislactim diethoxy ether as a highly stereo-inducing synthon for sterically hindered, γ-branched α-amino acids: A practical, large-scale route to an intermediate of the novel renin inhibitor aliskiren". . p. 2848 - 2870. Retrieved 2007/10/03.