5-fluoro-2-((S)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide

Base Information

• Chemical Name: 5-fluoro-2-((S)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide
• CAS No.: 1257648-84-2
• Molecular Formula: C₂₈H₃₅F₄NO₃Si
• Molecular Weight: 537.67
• Mol file: 1257648-84-2.mol

Synonyms:5-fluoro-2-((S)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide

Chemical Property of 5-fluoro-2-((S)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-fluoro-2-((S)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide

There total 12 articles about 5-fluoro-2-((S)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide 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: 76.0%

trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane (129217-85-2) + (S)-5-fluoro-N-(1-(4-methoxyphenyl)ethyl)-2-(5,5,5-trifluoro-2-methyl-4-oxopentan-2-yl)benzamide (1198785-54-4) → C28H35F4NO3Si + 5-fluoro-2-((S)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide (1257648-84-2) + 5-fluoro-2-((R)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide

Guidance literature:

With (S)-1-isopropyl-pyrrolidine-2-carboxylic acid; diethylzinc; In tetrahydrofuran; toluene; at -20 ℃; for 72h; Product distribution / selectivity; Inert atmosphere;

Reference yield:

trimethyl(prop-1-ynyl)silane (6224-91-5) + (S)-5-fluoro-N-(1-(4-methoxyphenyl)ethyl)-2-(5,5,5-trifluoro-2-methyl-4-oxopentan-2-yl)benzamide (1198785-54-4) → 5-fluoro-2-((S)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide (1257648-84-2) + 5-fluoro-2-((R)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide

Guidance literature:

trimethyl(prop-1-ynyl)silane; With n-butyllithium; In tetrahydrofuran; hexane; at -25 - -15 ℃; for 1h;

With zinc dibromide; In tetrahydrofuran; hexane; at -20 - -15 ℃; for 1h;

(S)-5-fluoro-N-(1-(4-methoxyphenyl)ethyl)-2-(5,5,5-trifluoro-2-methyl-4-oxopentan-2-yl)benzamide; In tetrahydrofuran; hexane; at -20 - -15 ℃; for 1h;

DOI:10.1021/jo400079z

Reference yield:

5-(2-(2-bromo-4-fluorophenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione (1429053-34-8) → 5-fluoro-2-((S)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide (1257648-84-2) + 5-fluoro-2-((R)-4-hydroxy-2-methyl-4-(trifluoromethyl)-7-(trimethylsilyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / N,N-dimethyl-formamide; water / 15 h / 100 °C / Large scale

2.1: pyridine / toluene / 12 h / 60 - 65 °C / Large scale

2.2: 1 h / 50 °C / Large scale

3.1: sodium hydride / tetrahydrofuran; mineral oil / 18 h / 0 - 25 °C / Large scale

3.2: 5 h / 0 - 25 °C / Large scale

3.3: 0.5 h / 0 - 15 °C / Large scale

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -25 - -15 °C

4.2: 1 h / -20 - -15 °C

4.3: 1 h / -20 - -15 °C

With pyridine; hydrogenchloride; n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1021/jo400079z

upstream raw materials:

trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane

(S)-5-fluoro-N-(1-(4-methoxyphenyl)ethyl)-2-(5,5,5-trifluoro-2-methyl-4-oxopentan-2-yl)benzamide

trimethyl(prop-1-ynyl)silane

2,2-dimethyl-5-(propan-2-ylidene)-1,3-dioxane-4,6-dione

Downstream raw materials:

5-fluoro-2-((S)-4-hydroxy-2-methyl-4-(trifluoromethyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide

5-fluoro-2-((R)-4-hydroxy-2-methyl-4-(trifluoromethyl)hept-6-yn-2-yl)-N-((S)-1-(4-methoxyphenyl)ethyl)benzamide