(S)-N-acetyl-3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(5-oxazolyl)propylamine

Base Information

Chemical Name:(S)-N-acetyl-3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(5-oxazolyl)propylamine
CAS No.:206195-35-9
Molecular Formula:C₁₉H₂₂N₂O₅
Molecular Weight:358.394
Hs Code.:

Synonyms:(S)-N-acetyl-3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(5-oxazolyl)propylamine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S)-N-acetyl-3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(5-oxazolyl)propylamine

Chemical Property:

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Technology Process of (S)-N-acetyl-3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(5-oxazolyl)propylamine

There total 6 articles about (S)-N-acetyl-3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(5-oxazolyl)propylamine 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: 64.0%

: 38622-91-2,36635-61-7
[(p-methylphenyl)sulfonylmethyl]isonitrile

: 1058131-94-4
N-[3-(2-ethynyl-3,4,5-trimethoxy-phenyl)-1-formyl-propyl]-acetamide

: 206195-35-9
(S)-N-acetyl-3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(5-oxazolyl)propylamine

Guidance literature:: [(p-methylphenyl)sulfonylmethyl]isonitrile; N-[3-(2-ethynyl-3,4,5-trimethoxy-phenyl)-1-formyl-propyl]-acetamide; With potassium carbonate; In methanol; for 1h; Heating;

With potassium hydroxide; In methanol; for 3h; Heating;
DOI:10.1016/S0040-4020(00)00862-0

Reference yield:

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: 206195-35-9
(S)-N-acetyl-3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(5-oxazolyl)propylamine

Guidance literature:: Multi-step reaction with 9 steps

1.1: zinc-copper couple / benzene; N,N-dimethyl-acetamide / 3 h / 20 °C / sonication

1.2: 31 percent / bis(triphenylphosphine)palladium dichloride / benzene; N,N-dimethyl-acetamide / 2 h / sonication

2.1: 91 percent / H₂ / Pd/C / ethanol; H₂O / 22 h / 3102.89 Torr

3.1: 93 percent / NaHCO₃; silver trifluoroacetate; I₂ / CHCl₃ / 2 h / 0 °C

4.1: trifluoroacetic acid / diethyl ether / 3 h / 20 °C

5.1: 454 mg / 4-(dimethylamino)pyridine; Et₃N / diethyl ether / 10 h

6.1: 60 percent / Et₂NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 15 h / 90 °C

7.1: 91 percent / potassium carbonate / methanol / 11 h / 20 °C

8.1: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

9.1: potassium carbonate / methanol / 1 h / Heating

9.2: 64 percent / KOH / methanol / 3 h / Heating

With dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; zinc copper; hydrogen; iodine; silver trifluoroacetate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; diethylamine; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; N,N-dimethyl acetamide; water; dimethyl sulfoxide; benzene; 6.1: Sonogashira coupling;
DOI:10.1016/S0040-4020(00)00862-0

Reference yield:

: (S)-2-Amino-4-(2-iodo-3,4,5-trimethoxy-phenyl)-butyric acid methyl ester

: 206195-35-9
(S)-N-acetyl-3-(2-ethynyl-3,4,5-trimethoxyphenyl)-1-(5-oxazolyl)propylamine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 454 mg / 4-(dimethylamino)pyridine; Et₃N / diethyl ether / 10 h

2.1: 60 percent / Et₂NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 15 h / 90 °C

3.1: 91 percent / potassium carbonate / methanol / 11 h / 20 °C

4.1: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

5.1: potassium carbonate / methanol / 1 h / Heating

5.2: 64 percent / KOH / methanol / 3 h / Heating

With dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisobutylaluminium hydride; potassium carbonate; diethylamine; triethylamine; In methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; 2.1: Sonogashira coupling;
DOI:10.1016/S0040-4020(00)00862-0