methyl (S)-2-azido-3-{[(S)-N-tert-butoxycarbonylphenylalanyl]-(tolyl-4'-sulfonyl)amino}propionate

Base Information

• Chemical Name: methyl (S)-2-azido-3-{[(S)-N-tert-butoxycarbonylphenylalanyl]-(tolyl-4'-sulfonyl)amino}propionate
• CAS No.: 1154035-32-1
• Molecular Formula: C₂₅H₃₁N₅O₇S
• Molecular Weight: 545.616
• Mol file: 1154035-32-1.mol

Synonyms:methyl (S)-2-azido-3-{[(S)-N-tert-butoxycarbonylphenylalanyl]-(tolyl-4'-sulfonyl)amino}propionate

Chemical Property of methyl (S)-2-azido-3-{[(S)-N-tert-butoxycarbonylphenylalanyl]-(tolyl-4'-sulfonyl)amino}propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S)-2-azido-3-{[(S)-N-tert-butoxycarbonylphenylalanyl]-(tolyl-4'-sulfonyl)amino}propionate

There total 5 articles about methyl (S)-2-azido-3-{[(S)-N-tert-butoxycarbonylphenylalanyl]-(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: 80.0%

(S)-2-azido-3-(4’-tolyl-sulfonylamino)-propionic acid methyl ester (1154035-19-4) + 1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-phenylethyl)carbamate (133010-06-7) → methyl (S)-2-azido-3-{[(S)-N-tert-butoxycarbonylphenylalanyl]-(tolyl-4'-sulfonyl)amino}propionate (1154035-32-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃;

DOI:10.1039/b822436f

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → methyl (S)-2-azido-3-{[(S)-N-tert-butoxycarbonylphenylalanyl]-(tolyl-4'-sulfonyl)amino}propionate (1154035-32-1)

Guidance literature:

Multi-step reaction with 4 steps

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

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

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

4: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With thionyl chloride; triflic azide; sodium hydrogencarbonate; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201300160

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-(tolyl-4'-sulfonylamino)-propionic acid (72071-27-3) → methyl (S)-2-azido-3-{[(S)-N-tert-butoxycarbonylphenylalanyl]-(tolyl-4'-sulfonyl)amino}propionate (1154035-32-1)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With thionyl chloride; triflic azide; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201300160

upstream raw materials:

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

1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-phenylethyl)carbamate

p-toluenesulfonyl chloride

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

Downstream raw materials:

C₂₆H₃₁N₃O₇S