2-(3-chlorophenoxy)-3-methoxy-4-{(1R)-1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid

Base Information

• Chemical Name: 2-(3-chlorophenoxy)-3-methoxy-4-{(1R)-1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid
• CAS No.: 1612223-76-3
• Molecular Formula: C₂₇H₃₀ClN₃O₆
• Molecular Weight: 528.005
• Mol file: 1612223-76-3.mol

Synonyms:

Chemical Property of 2-(3-chlorophenoxy)-3-methoxy-4-{(1R)-1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(3-chlorophenoxy)-3-methoxy-4-{(1R)-1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid

There total 7 articles about 2-(3-chlorophenoxy)-3-methoxy-4-{(1R)-1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid 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: 30.0%

2-(3-chlorophenoxy)-3-methoxy-4-{1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid (1612223-69-4) → 2-(3-chlorophenoxy)-3-methoxy-4-{(1R)-1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid (1612223-76-3) + 2-(3-chlorophenoxy)-3-methoxy-4-{(1S)-1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid (1612223-77-4)

Guidance literature:

With diethylamine; In methanol; ethanol; hexane; Resolution of racemate;

DOI:10.1021/jm500463c

Reference yield:

4-bromo-3-(3-chlorophenoxy)-2-methoxybenzaldehyde (1612223-64-9) → 2-(3-chlorophenoxy)-3-methoxy-4-{(1R)-1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid (1612223-76-3) + 2-(3-chlorophenoxy)-3-methoxy-4-{(1S)-1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid (1612223-77-4)

Guidance literature:

Multi-step reaction with 6 steps

1: diethyl ether / 2 h / -78 °C

2: triethylamine / dichloromethane / 2 h / 0 - 20 °C

3: acetonitrile / 80 °C

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 0.75 h / 20 - 110 °C / Inert atmosphere; Microwave irradiation

5: sodium hydroxide / ethanol / 12 h / Reflux

6: diethylamine / ethanol; methanol; hexane / Resolution of racemate

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamine; triethylamine; sodium hydroxide; In methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm500463c

Reference yield:

1-[4-bromo-3-(3-chlorophenoxy)-2-methoxyphenyl]propan-1-ol (1612223-65-0) → 2-(3-chlorophenoxy)-3-methoxy-4-{(1R)-1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid (1612223-76-3) + 2-(3-chlorophenoxy)-3-methoxy-4-{(1S)-1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid (1612223-77-4)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / dichloromethane / 2 h / 0 - 20 °C

2: acetonitrile / 80 °C

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 0.75 h / 20 - 110 °C / Inert atmosphere; Microwave irradiation

4: sodium hydroxide / ethanol / 12 h / Reflux

5: diethylamine / ethanol; methanol; hexane / Resolution of racemate

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamine; triethylamine; sodium hydroxide; In methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm500463c

upstream raw materials:

4-bromo-3-(3-chlorophenoxy)-2-methoxybenzaldehyde

1-[4-bromo-3-(3-chlorophenoxy)-2-methoxyphenyl]propan-1-ol

1-[(3S)-1-{1-[4-bromo-3-(3-chlorophenoxy)-2-methoxyphenyl]propyl}piperidin-3-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

2-(3-chlorophenoxy)-3-methoxy-4-{1-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)piperidin-1-yl]propyl}benzoic acid