N-((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxy propan-2-yl)-2-(1H-indol-3-yl)-2-oxoacetamide

Base Information

Chemical Name:N-((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxy propan-2-yl)-2-(1H-indol-3-yl)-2-oxoacetamide
CAS No.:1350705-72-4
Molecular Formula:C₂₈H₃₅N₃O₅Si
Molecular Weight:521.688
Hs Code.:

Synonyms:N-((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxy propan-2-yl)-2-(1H-indol-3-yl)-2-oxoacetamide

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Chemical Property of N-((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxy propan-2-yl)-2-(1H-indol-3-yl)-2-oxoacetamide

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Technology Process of N-((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxy propan-2-yl)-2-(1H-indol-3-yl)-2-oxoacetamide

There total 10 articles about N-((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxy propan-2-yl)-2-(1H-indol-3-yl)-2-oxoacetamide 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: 70.0%

: 22980-09-2
indolyl-3-glyoxylyl chloride

: 1350705-71-3
C₁₈H₃₀N₂O₃Si

: 1350705-72-4
N-((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxy propan-2-yl)-2-(1H-indol-3-yl)-2-oxoacetamide

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; Reflux;
DOI:10.1039/c3ra44631j

Reference yield:

: 120-72-9
indole

: 1350705-72-4
N-((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxy propan-2-yl)-2-(1H-indol-3-yl)-2-oxoacetamide

Guidance literature:: Multi-step reaction with 2 steps

1: diethyl ether / 0.5 h / 0 °C / Inert atmosphere

2: triethylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

With triethylamine; In diethyl ether; dichloromethane;
DOI:10.1039/c1ob06320k

Reference yield:

: 4397-53-9
p-benzyloxybenzaldehyde

: 1350705-72-4
N-((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(4-(2-cyanoethoxy)phenyl)-3-hydroxy propan-2-yl)-2-(1H-indol-3-yl)-2-oxoacetamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: water / 2 h / 90 °C / Inert atmosphere

2.1: tert-butylhypochlorite; sodium hydroxide / propan-1-ol; water / 0.08 h / Inert atmosphere

2.2: 2 h / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

4.1: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C / Inert atmosphere

5.1: N-benzyl-trimethylammonium hydroxide / 8 h / Reflux; Inert atmosphere

6.1: lithium borohydride / methanol; diethyl ether / 4 h / 20 °C / Inert atmosphere

7.1: ytterbium(III) triflate / dichloromethane / 8 h / Inert atmosphere; Reflux

8.1: triethylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; lithium borohydride; tert-butylhypochlorite; 5%-palladium/activated carbon; hydrogen; N-benzyl-trimethylammonium hydroxide; triethylamine; sodium hydroxide; ytterbium(III) triflate; In methanol; propan-1-ol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 5.1: Michael reaction;
DOI:10.1039/c1ob06320k