3-Azetidinecarboxylic acid, 1-[[3,4-dihydro-1-methyl-6-(4-phenylbutoxy)-2-naphthalenyl]methyl]-

Base Information

• Chemical Name: 3-Azetidinecarboxylic acid, 1-[[3,4-dihydro-1-methyl-6-(4-phenylbutoxy)-2-naphthalenyl]methyl]-
• CAS No.: 847586-08-7
• Molecular Formula: C26H31NO3
• Molecular Weight: 405.537
• Mol file: 847586-08-7.mol

Synonyms:

Chemical Property of 3-Azetidinecarboxylic acid, 1-[[3,4-dihydro-1-methyl-6-(4-phenylbutoxy)-2-naphthalenyl]methyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Azetidinecarboxylic acid, 1-[[3,4-dihydro-1-methyl-6-(4-phenylbutoxy)-2-naphthalenyl]methyl]-

There total 9 articles about 3-Azetidinecarboxylic acid, 1-[[3,4-dihydro-1-methyl-6-(4-phenylbutoxy)-2-naphthalenyl]methyl]- 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: 80.0%

[1-methyl-6-(4-phenylbutoxy)-3,4-dihydronaphthalen-2-yl]bromomethane + 3-azetidinecarboxylic acid (36476-78-5) → 1-{[1-methyl-6-(4-phenylbutoxy)-3,4-dihydronaphthalen-2-yl]methyl}azetidine-3-carboxylic acid (847586-08-7)

Guidance literature:

[1-methyl-6-(4-phenylbutoxy)-3,4-dihydronaphthalen-2-yl]bromomethane; In N,N-dimethyl-formamide; at 25 - 30 ℃; for 0.5h;

3-azetidinecarboxylic acid; In N,N-dimethyl-formamide;

With potassium carbonate; In N,N-dimethyl-formamide; at 38 - 42 ℃;

Reference yield:

6-(4-phenylbutoxy)-3,4-dihydronaphthalen-1(2H)-one (847585-55-1) → 1-{[1-methyl-6-(4-phenylbutoxy)-3,4-dihydronaphthalen-2-yl]methyl}azetidine-3-carboxylic acid (847586-08-7)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran; diethyl ether

2: toluene-4-sulfonic acid / dichloromethane; water

3: trichlorophosphate / dichloromethane

4: sodium sulfate / tetrahydrofuran; methanol; isopropyl alcohol

With toluene-4-sulfonic acid; sodium sulfate; trichlorophosphate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; isopropyl alcohol;

DOI:10.1016/j.bmcl.2011.05.029

Reference yield:

C21H26O2 (1314760-19-4) → 1-{[1-methyl-6-(4-phenylbutoxy)-3,4-dihydronaphthalen-2-yl]methyl}azetidine-3-carboxylic acid (847586-08-7)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / dichloromethane; water

2: trichlorophosphate / dichloromethane

3: sodium sulfate / tetrahydrofuran; methanol; isopropyl alcohol

With toluene-4-sulfonic acid; sodium sulfate; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol;

DOI:10.1016/j.bmcl.2011.05.029

upstream raw materials:

6-(4-phenylbutoxy)-3,4-dihydronaphthalen-1(2H)-one

C₂₁H₂₆O₂

4-methyl-7-(4-phenylbutoxy)-1,2-dihydronaphthalene

C₂₂H₂₄O₂

Downstream raw materials:

1-{[1-methyl-6-(4-phenylbutoxy)-3,4-dihydro-2-naphthalenyl]methyl}-3-azetidinecarboxylic acid hydrochloride

Refernces

• 1、 Kurata, Haruto,Kusumi, Kensuke,Otsuki, Kazuhiro,Suzuki, Ryo,Kurono, Masakuni,Takada, Yuka,Shioya, Hiroki,Komiya, Takaki,Mizuno, Hirotaka,Ono, Takeji,Hagiya, Hiroshi,Minami, Masashi,Nakade, Shinji,Habashita, Hiromu. "Discovery of S1P agonists with a dihydronaphthalene scaffold". . p. 3885 - 3889. Retrieved 2011/08/06.