isobutyric acid 2-((R)-3-diisopropylammonium-1-phenyIpropyl)-4-(hydroxymethyl)phenyl ester (R)-acetoxy(phenyl)acetate

Base Information

• Chemical Name: isobutyric acid 2-((R)-3-diisopropylammonium-1-phenyIpropyl)-4-(hydroxymethyl)phenyl ester (R)-acetoxy(phenyl)acetate
• CAS No.: 1390644-34-4
• Molecular Formula: C₁₀H₁₀O₄*C₂₆H₃₇NO₃
• Molecular Weight: 605.772
• Mol file: 1390644-34-4.mol

Synonyms:

Chemical Property of isobutyric acid 2-((R)-3-diisopropylammonium-1-phenyIpropyl)-4-(hydroxymethyl)phenyl ester (R)-acetoxy(phenyl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of isobutyric acid 2-((R)-3-diisopropylammonium-1-phenyIpropyl)-4-(hydroxymethyl)phenyl ester (R)-acetoxy(phenyl)acetate

There total 24 articles about isobutyric acid 2-((R)-3-diisopropylammonium-1-phenyIpropyl)-4-(hydroxymethyl)phenyl ester (R)-acetoxy(phenyl)acetate 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:

fesoterodine (286930-02-7,250214-44-9) + (R)-(-)-O-acetylmandelic acid (51019-43-3) → isobutyric acid 2-((R)-3-diisopropylammonium-1-phenyIpropyl)-4-(hydroxymethyl)phenyl ester (R)-acetoxy(phenyl)acetate (1390644-34-4)

Guidance literature:

In ethyl acetate; for 0.5h; Reflux;

Reference yield:

(R)-(-)-3-(3-diisopropylamino-1-phenylpropyl)-4-hydroxybenzoic acid methyl ester (214601-16-8) → isobutyric acid 2-((R)-3-diisopropylammonium-1-phenyIpropyl)-4-(hydroxymethyl)phenyl ester (R)-acetoxy(phenyl)acetate (1390644-34-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 2 h / 0 - 5 °C / Inert atmosphere

2: sodium hydrogencarbonate / dichloromethane; water / 0.5 h / 0 - 5 °C / Inert atmosphere

3: ethyl acetate / 0.5 h / Reflux

With sodium hydrogencarbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

Reference yield:

(+/-)-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropane-1-ol → isobutyric acid 2-((R)-3-diisopropylammonium-1-phenyIpropyl)-4-(hydroxymethyl)phenyl ester (R)-acetoxy(phenyl)acetate (1390644-34-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 5 °C

2.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere

3.1: isopropyl alcohol / 30 - 55 °C

4.1: sodium hydroxide; water / dichloromethane / 0.25 h / 10 - 20 °C / pH 11.5

4.2: 4 h / 25 - 55 °C / Inert atmosphere

4.3: -70 - -10 °C / Inert atmosphere

5.1: thionyl chloride / 5 h / 40 - 45 °C

6.1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 18 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave

7.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 2 h / 0 - 5 °C / Inert atmosphere

8.1: chloroform / 0.75 h / -45 - -35 °C

9.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 6 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave

10.1: ethyl acetate / 0.5 h / Reflux

With dmap; thionyl chloride; water; hydrogen; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium hydroxide; 5%-palladium/activated carbon; palladium 10% on activated carbon; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; isopropyl alcohol; acetonitrile;

upstream raw materials:

methyl 4-(benzyloxy)-3-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]benzoate

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol

(R)-(-)-3-(3-diisopropylamino-1-phenylpropyl)-4-hydroxybenzoic acid methyl ester

4-hydroxy-benzoic acid

Downstream raw materials:

fesoterodine fumarate

Refernces