methyl (S)-2-azido-3-[(naphth-1-ylcarbonyl)(tolyl-4'-sulfonyl)-amino]propionate

Base Information

Chemical Name:methyl (S)-2-azido-3-[(naphth-1-ylcarbonyl)(tolyl-4'-sulfonyl)-amino]propionate
CAS No.:1154035-29-6
Molecular Formula:C₂₂H₂₀N₄O₅S
Molecular Weight:452.491
Hs Code.:

Synonyms:methyl (S)-2-azido-3-[(naphth-1-ylcarbonyl)(tolyl-4'-sulfonyl)-amino]propionate

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Chemical Property of methyl (S)-2-azido-3-[(naphth-1-ylcarbonyl)(tolyl-4'-sulfonyl)-amino]propionate

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Technology Process of methyl (S)-2-azido-3-[(naphth-1-ylcarbonyl)(tolyl-4'-sulfonyl)-amino]propionate

There total 4 articles about methyl (S)-2-azido-3-[(naphth-1-ylcarbonyl)(tolyl-4'-sulfonyl)-amino]propionate 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: 85.0%

: 86-55-5
1-naphthalenecarboxylic acid

: 1154035-19-4
(S)-2-azido-3-(4’-tolyl-sulfonylamino)-propionic acid methyl ester

: 1154035-29-6
methyl (S)-2-azido-3-[(naphth-1-ylcarbonyl)(tolyl-4'-sulfonyl)-amino]propionate

Guidance literature:: 1-naphthalenecarboxylic acid; With caesium carbonate; HATU; In dichloromethane; at 0 ℃; for 0.25h;

(S)-2-azido-3-(4’-tolyl-sulfonylamino)-propionic acid methyl ester; In dichloromethane; at 0 ℃;
DOI:10.1039/b822436f

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 1154035-29-6
methyl (S)-2-azido-3-[(naphth-1-ylcarbonyl)(tolyl-4'-sulfonyl)-amino]propionate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydrogencarbonate; sodium hydroxide / water; 1,4-dioxane / 2.5 h / 0 - 20 °C / pH 9 / Inert atmosphere

2.1: thionyl chloride / 6 h / 0 - 20 °C / Inert atmosphere

3.1: triflic azide; triethylamine; copper(II) sulfate / methanol; water; dichloromethane / 20 °C / Inert atmosphere

4.1: caesium carbonate; HATU / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

4.2: 0 °C / Inert atmosphere

With thionyl chloride; triflic azide; sodium hydrogencarbonate; caesium carbonate; copper(II) sulfate; triethylamine; HATU; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water;
DOI:10.1002/ejoc.201300160

Reference yield:

: 72071-27-3
(S)-2-tert-butoxycarbonylamino-3-(tolyl-4'-sulfonylamino)-propionic acid

: 1154035-29-6
methyl (S)-2-azido-3-[(naphth-1-ylcarbonyl)(tolyl-4'-sulfonyl)-amino]propionate

Guidance literature:: Multi-step reaction with 3 steps

1.1: thionyl chloride / 6 h / 0 - 20 °C / Inert atmosphere

2.1: triflic azide; N-ethyl-N,N-diisopropylamine; copper(II) sulfate / dichloromethane; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

3.1: caesium carbonate; HATU / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

With thionyl chloride; triflic azide; caesium carbonate; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201300160