3-[(tert-butoxycarbonyl)amino]-5-[3-(trimethylsilyl)prop-2-yn-1-yl]benzoic acid

Base Information

Chemical Name:3-[(tert-butoxycarbonyl)amino]-5-[3-(trimethylsilyl)prop-2-yn-1-yl]benzoic acid
CAS No.:1639866-77-5
Molecular Formula:C₁₈H₂₅NO₄Si
Molecular Weight:347.486
Hs Code.:

Synonyms:3-[(tert-butoxycarbonyl)amino]-5-[3-(trimethylsilyl)prop-2-yn-1-yl]benzoic acid

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Chemical Property of 3-[(tert-butoxycarbonyl)amino]-5-[3-(trimethylsilyl)prop-2-yn-1-yl]benzoic acid

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Technology Process of 3-[(tert-butoxycarbonyl)amino]-5-[3-(trimethylsilyl)prop-2-yn-1-yl]benzoic acid

There total 5 articles about 3-[(tert-butoxycarbonyl)amino]-5-[3-(trimethylsilyl)prop-2-yn-1-yl]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: 92.0%

: 1639866-76-4
tert-butyl {3-hydroxymethyl-5-[3-(trimethylsilyl)prop-2-yn-1-yl]phenyl}carbamate

: 1639866-77-5
3-[(tert-butoxycarbonyl)amino]-5-[3-(trimethylsilyl)prop-2-yn-1-yl]benzoic acid

Guidance literature:: With Jones reagent; In acetone; at 20 ℃; for 4.5h;
DOI:10.3762/bjoc.10.49

Reference yield:

: 220286-47-5
3-Amino-5-hydroxymethylbenzoic acid methyl ester

: 1639866-77-5
3-[(tert-butoxycarbonyl)amino]-5-[3-(trimethylsilyl)prop-2-yn-1-yl]benzoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: ethanol / 20 h / 30 °C

2.1: triphenylphosphine; 1H-imidazole; bromine / dichloromethane / 2.5 h / 0 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / -7 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

3.3: 20 h / 65 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane; hexane / 22 h / -55 - 20 °C

5.1: Jones reagent / acetone / 4.5 h / 20 °C

With 1H-imidazole; Jones reagent; n-butyllithium; bromine; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetone;
DOI:10.3762/bjoc.10.49

Reference yield:

: 1955-46-0
5-nitro-1,3-benzenedicarboxylic acid, monomethyl ester

: 1639866-77-5
3-[(tert-butoxycarbonyl)amino]-5-[3-(trimethylsilyl)prop-2-yn-1-yl]benzoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 0.25 h / -10 - 80 °C

2.1: palladium 10% on activated carbon; hydrogen / ethanol / 8 h

3.1: ethanol / 20 h / 30 °C

4.1: triphenylphosphine; 1H-imidazole; bromine / dichloromethane / 2.5 h / 0 - 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / -7 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

5.3: 20 h / 65 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane; hexane / 22 h / -55 - 20 °C

7.1: Jones reagent / acetone / 4.5 h / 20 °C

With 1H-imidazole; Jones reagent; n-butyllithium; dimethylsulfide borane complex; palladium 10% on activated carbon; hydrogen; bromine; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetone;
DOI:10.3762/bjoc.10.49