6-Heptynoic acid, 7-(2-aminophenyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester, (2S)-

Base Information

• Chemical Name: 6-Heptynoic acid, 7-(2-aminophenyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester, (2S)-
• CAS No.: 540517-07-5
• Molecular Formula: C19H26N2O4
• Molecular Weight: 346.426
• Mol file: 540517-07-5.mol

Synonyms:

Chemical Property of 6-Heptynoic acid, 7-(2-aminophenyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester, (2S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-Heptynoic acid, 7-(2-aminophenyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester, (2S)-

There total 4 articles about 6-Heptynoic acid, 7-(2-aminophenyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester, (2S)- 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: 78.0%

2-iodophenylamine (615-43-0) + methyl (2S)-2-[(tert-butoxycarbonyl)amino]-6-heptynoate (540517-06-4) → methyl (2S)-7-(2-aminophenyl)-2-[(tert-butoxycarbonyl)amino]-5-heptynoate (540517-07-5)

Guidance literature:

With copper(l) iodide; diethylamine; bis-triphenylphosphine-palladium(II) chloride; In diethyl ether; at 20 ℃; for 3h;

DOI:10.1021/ol034360d

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → methyl (2S)-7-(2-aminophenyl)-2-[(tert-butoxycarbonyl)amino]-5-heptynoate (540517-07-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.33 g / NaHCO₃ / dioxane; H₂O / 4 h / 20 °C

2: 78 percent / CuI; Et₂NH / PdCl₂(PPh₃)2 / diethyl ether / 2 h / 20 °C

With copper(l) iodide; sodium hydrogencarbonate; diethylamine; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; diethyl ether; water; 2: Sonogashira cross-coupling;

DOI:10.1002/adsc.200404012

Reference yield:

(S)-bishomopropargylglycine (121703-79-5,211054-03-4,835627-45-7) → methyl (2S)-7-(2-aminophenyl)-2-[(tert-butoxycarbonyl)amino]-5-heptynoate (540517-07-5)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂ / 4 h / Heating

2: 1.33 g / NaHCO₃ / dioxane; H₂O / 4 h / 20 °C

3: 78 percent / CuI; Et₂NH / PdCl₂(PPh₃)2 / diethyl ether / 2 h / 20 °C

With copper(l) iodide; thionyl chloride; sodium hydrogencarbonate; diethylamine; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; diethyl ether; water; 3: Sonogashira cross-coupling;

DOI:10.1002/adsc.200404012

upstream raw materials:

2-iodophenylamine

methyl (2S)-2-[(tert-butoxycarbonyl)amino]-6-heptynoate

di-tert-butyl dicarbonate

(S)-bishomopropargylglycine

Refernces

• 1、 Van Esseveldt, Bart C. J.,Van Delft, Floris L.,De Gelder, Rene,Rutjes, Floris P. J. T.. "Palladium-catalyzed synthesis of novel optically active tryptophan analogues". . p. 1717 - 1720. Retrieved 2007/10/03.