methyl 2-((S)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate

Base Information

• Chemical Name: methyl 2-((S)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate
• CAS No.: 1093864-97-1
• Molecular Formula: C₂₇H₃₅ClFN₃O₅
• Molecular Weight: 536.043
• Mol file: 1093864-97-1.mol

Synonyms:methyl 2-((S)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate

Chemical Property of methyl 2-((S)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-((S)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate

There total 34 articles about methyl 2-((S)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate 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:

[2-{3-[(3-chloro-5-fluoro-phenyl)-((S)-2-methoxycarbonylamino-ethoxy)-methyl]-benzoylamino}-1-((R)-tetrahydro-pyran-3-ylmethyl)-ethyl]-methyl-carbamic acid tert-butyl ester (1093865-63-4) → methyl 2-((S)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate (1093864-97-1) + methyl 2-((R)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate (1093864-96-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 0 ℃; for 1h;

Reference yield:

N-(2-((R)-tetrahydro-2H-pyran-3-yl)-eth-(E)-ylidene)methanamine (1013937-83-1) → methyl 2-((S)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate (1093864-97-1) + methyl 2-((R)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate (1093864-96-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 3-{(E)-[((1R,2R)-2-{[({(1S)-1-[(dimethylamino)carbonyl]-2,2-dimethylpropyl}amino)carbonothioyl]amino}cyclohexyl)imino]methyl}-5-(1,1-dimethylethyl)-4-hydroxyphenyl 2,2-dimethylpropanoate / toluene / 0.25 h / -78 °C

1.2: 4.17 h / -78 - 20 °C

2.1: ammonia; hydrogen / nickel / methanol / 0.5 h / 14 - 25 °C / 22801.5 Torr

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C

4.1: hydrogenchloride / 1,4-dioxane / 1 h / 0 °C

With hydrogenchloride; ammonia; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-{(E)-[((1R,2R)-2-{[({(1S)-1-[(dimethylamino)carbonyl]-2,2-dimethylpropyl}amino)carbonothioyl]amino}cyclohexyl)imino]methyl}-5-(1,1-dimethylethyl)-4-hydroxyphenyl 2,2-dimethylpropanoate; nickel; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene;

Reference yield:

5-Chlorovaleroyl chloride (1575-61-7) → methyl 2-((S)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate (1093864-97-1) + methyl 2-((R)-(3-chloro-5-fluorophenyl)(3-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)phenyl)methoxy)ethylcarbamate (1093864-96-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine / tetrahydrofuran / 1.25 h / 0 - 20 °C

2.1: n-butyllithium; diisopropylamine; lithium chloride / tetrahydrofuran; hexane / 3 h / -78 - 0 °C

2.2: 0.87 h / 0 - 20 °C

3.1: n-butyllithium; borane-ammonia complex; diisopropylamine / tetrahydrofuran; hexane / 4.08 h / -78 - 20 °C

3.2: -10 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 2.92 h / 5 - 20 °C

5.1: ruthenium trichloride / water; acetonitrile / 0.08 h / 20 °C

5.2: 0.5 h / 20 °C

6.1: tetrahydrofuran / 1 h / 20 °C / Molecular sieve

7.1: 3-{(E)-[((1R,2R)-2-{[({(1S)-1-[(dimethylamino)carbonyl]-2,2-dimethylpropyl}amino)carbonothioyl]amino}cyclohexyl)imino]methyl}-5-(1,1-dimethylethyl)-4-hydroxyphenyl 2,2-dimethylpropanoate / toluene / 0.25 h / -78 °C

7.2: 4.17 h / -78 - 20 °C

8.1: ammonia; hydrogen / nickel / methanol / 0.5 h / 14 - 25 °C / 22801.5 Torr

9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C

10.1: hydrogenchloride / 1,4-dioxane / 1 h / 0 °C

With hydrogenchloride; n-butyllithium; borane-ammonia complex; ammonia; hydrogen; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; ruthenium trichloride; 3-{(E)-[((1R,2R)-2-{[({(1S)-1-[(dimethylamino)carbonyl]-2,2-dimethylpropyl}amino)carbonothioyl]amino}cyclohexyl)imino]methyl}-5-(1,1-dimethylethyl)-4-hydroxyphenyl 2,2-dimethylpropanoate; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

[2-{3-[(3-chloro-5-fluoro-phenyl)-((S)-2-methoxycarbonylamino-ethoxy)-methyl]-benzoylamino}-1-((R)-tetrahydro-pyran-3-ylmethyl)-ethyl]-methyl-carbamic acid tert-butyl ester

5-Chlorovaleroyl chloride

(R)-2-(tetrahydro-2H-pyran-3-yl)-acetaldehyde

(R)-3-allyl-tetrahydro-2H-pyran