4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene

Base Information

• Chemical Name: 4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene
• CAS No.: 324763-39-5
• Molecular Formula: C17H27ClO3
• Molecular Weight: 314.853
• Hs Code.: 2909309090
• European Community (EC) Number: 608-745-9
• DSSTox Substance ID: DTXSID20466306
• Nikkaji Number: J1.450.708F
• Wikidata: Q72454210
• Mol file: 324763-39-5.mol

Synonyms:324763-39-5;(R)-4-(2-(chloromethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene;4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene;Benzene, 4-[(2R)-2-(chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)-;SCHEMBL188718;DTXSID20466306;MFCD11113214;AKOS015852573;AKOS015890623;AC-8338;AS-18671;AM20090743;CS-0363165;P11095

Chemical Property of 4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.491
• Boiling Point: 398.462 °C at 760 mmHg
• Flash Point: 122.153 °C
• PSA: 27.69000
• Density: 1.035 g/cm³
• LogP: 4.16400
• Storage Temp.: 2-8°C
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 314.1648724
• Heavy Atom Count: 21
• Complexity: 260

Purity/Quality:

99% ^*data from raw suppliers

4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CC1=CC(=C(C=C1)OC)OCCCOC)CCl
• Isomeric SMILES: CC(C)[C@@H](CC1=CC(=C(C=C1)OC)OCCCOC)CCl
• Uses: 4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene is an intermediate in the preparation of orally active renin inhibitor Aliskiren (A536000).

Technology Process of 4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene

There total 23 articles about 4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene 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: 82.0%

(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol (172900-70-8) → (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane (324763-39-5)

Guidance literature:

With tetrachloromethane; TOP; at 20 ℃; for 16h; trioctylphosphine was added at 10 °ree;C;

Reference yield: 64.0%

2-(3-(3-methoxypropoxy)-4-methoxybenzyl)-3-methylbutanol (943349-14-2) → (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane (324763-39-5)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In toluene; at 90 ℃; for 2h; Product distribution / selectivity;

Reference yield:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane (324763-39-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 82 percent

2.1: H₂ / Pd/C / ethyl acetate / 20 °C

3.1: (COCl)2 / dimethylformamide / 20 °C

4.1: NaOH / toluene / 20 °C

5.1: LDA; LiCl / tetrahydrofuran / 0 °C

5.2: tetrahydrofuran / 20 °C / Heating

6.1: 66 percent / BH₃*NH₃; n-BuLi / tetrahydrofuran / 20 °C

7.1: POCl₃; DMF / toluene / 80 °C

With sodium hydroxide; n-butyllithium; borane-ammonia complex; oxalyl dichloride; hydrogen; N,N-dimethyl-formamide; lithium chloride; lithium diisopropyl amide; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; toluene; 1.1: Knoevenagel condensation;

DOI:10.1016/S0040-4039(00)01760-3

upstream raw materials:

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

4-methoxy-3-(3-methoxypropoxy)benzaldehyde

(E)-3-[4-Methoxy-3-(3-methoxy-propoxy)-phenyl]-acrylic acid

(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid

Downstream raw materials:

(R)--4-(2-(iodomethyl)--3--methylbutyl)--1--methoxy-2--(3--methoxypropoxy)benzene

C₁₇H₂₇ClMgO₃

(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

(2S,7R,E)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-N,N,8-trimethylnon-4-enamide

Refernces

• 1、 -. "NOVEL PROCESS FOR THE PREPARATION OF RENIN INHIBITORS". Page/Page column 13. . Retrieved 2013/08/28.
• 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". Page/Page column 63. . Retrieved 2011/12/14.