methyl 4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoate

Base Information

• Chemical Name: methyl 4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoate
• CAS No.: 922161-75-9
• Molecular Formula: C₂₉H₄₀ClNO₇
• Molecular Weight: 550.092

Synonyms:methyl 4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoate

Chemical Property of methyl 4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl 4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoate

There total 10 articles about methyl 4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoate 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: 99.0%

3-(5-chloro-2-[(2,2-dimethylpropyl)amino]-3-[(S)-hydroxy-(2-methoxyphenyl)methyl]phenoxy)-2,2-dimethylpropan-1-ol (922163-01-7) + succinic acid monomethylester chloride (1490-25-1) → methyl 4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoate (922161-75-9)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 1h; Cooling with ice;

DOI:10.1016/j.bmc.2011.07.007

Reference yield:

2-(3-([tert-butyl(dimethyl)silyl]oxy)-2,2-dimethylpropoxy)-4-chloroaniline (922162-96-7) → methyl 4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoate (922161-75-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dmap; triethylamine / dichloromethane / 16 h / 0 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice

3.1: sec.-butyllithium / tetrahydrofuran; hexane; cyclohexane / 0.5 h / -78 - 20 °C

3.2: 1.5 h / -78 - -50 °C

4.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 4 h / 0 - 50 °C

4.2: 0.08 h

5.1: Chiralcel OD column / hexane; isopropyl alcohol / 20 °C / Resolution of racemate; HPLC conditions

6.1: sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Cooling with ice

With dmap; tetrabutyl ammonium fluoride; sec.-butyllithium; sodium hydrogencarbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; isopropyl alcohol; toluene;

DOI:10.1016/j.bmc.2011.07.007

Reference yield:

tert-butyl[3-(5-chloro-2-nitrophenoxy)-2,2-dimethylpropoxy]dimethylsilane (922162-95-6) → methyl 4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoate (922161-75-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hydrogen / ethyl acetate / 7 h / 20 °C

2.1: dmap; triethylamine / dichloromethane / 16 h / 0 - 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice

4.1: sec.-butyllithium / tetrahydrofuran; hexane; cyclohexane / 0.5 h / -78 - 20 °C

4.2: 1.5 h / -78 - -50 °C

5.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 4 h / 0 - 50 °C

5.2: 0.08 h

6.1: Chiralcel OD column / hexane; isopropyl alcohol / 20 °C / Resolution of racemate; HPLC conditions

7.1: sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Cooling with ice

With dmap; tetrabutyl ammonium fluoride; hydrogen; sec.-butyllithium; sodium hydrogencarbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; ethyl acetate; isopropyl alcohol; toluene;

DOI:10.1016/j.bmc.2011.07.007

upstream raw materials:

tert-butyl[3-(5-chloro-2-nitrophenoxy)-2,2-dimethylpropoxy]dimethylsilane

2-(3-([tert-butyl(dimethyl)silyl]oxy)-2,2-dimethylpropoxy)-4-chloroaniline

N-[2-(3-([tert-butyl(dimethyl)silyl]oxy)-2,2-dimethylpropoxy)-4-chlorophenyl]-2,2-dimethylpropanamide

N-[4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-phenyl]-2,2-dimethylpropanamide

Downstream raw materials:

4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid

ethyl (3S)-1-(4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

(3S)-1-(4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)-(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylicacid

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