3-{2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-[2-(6-methylamino-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

Base Information

• Chemical Name: 3-{2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-[2-(6-methylamino-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester
• CAS No.: 801239-46-3
• Molecular Formula: C₄₃H₆₃N₅O₁₀S
• Molecular Weight: 842.067
• Mol file: 801239-46-3.mol

Synonyms:3-{2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-[2-(6-methylamino-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

Chemical Property of 3-{2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-[2-(6-methylamino-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-[2-(6-methylamino-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

There total 8 articles about 3-{2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-[2-(6-methylamino-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester 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: 69.0%

3S-3-amino-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid tert-butyl ester (185563-98-8) + 2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-[2-(6-methylamino-pyridin-2-yl)-ethyl]-benzoic acid (801239-93-0) → 3-{2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-[2-(6-methylamino-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester (801239-46-3)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/jm049666k

Reference yield:

methyl 4-iodosalicylate (18179-39-0) → 3-{2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-[2-(6-methylamino-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester (801239-46-3)

Guidance literature:

Multi-step reaction with 7 steps

1: PPh₃; DIAD / CH₂Cl₂ / 16 h / 0 - 20 °C

2: 95 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / various solvent(s)

3: 75 percent / K₂CO₃ / methanol / 2 h / 20 °C

4: 85 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / various solvent(s) / 16 h / 90 °C

5: 54 percent / H₂ / Pd/C / ethanol / 16 h

6: 93 percent / aq. NaOH / tetrahydrofuran; methanol / 16 h

7: 69 percent / EDC; HOBT; NMM / dimethylformamide / 16 h / 20 °C

With 4-methyl-morpholine; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; di-isopropyl azodicarboxylate; hydrogen; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Mitsunobu reaction / 2: Sonogashira coupling / 4: Sonogashira coupling;

DOI:10.1021/jm049666k

Reference yield:

tert-butyl N-[3-[2-(2-hydroxyethoxy)ethoxy]propyl]carbamate → 3-{2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-[2-(6-methylamino-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester (801239-46-3)

Guidance literature:

Multi-step reaction with 7 steps

1: PPh₃; DIAD / CH₂Cl₂ / 16 h / 0 - 20 °C

2: 95 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / various solvent(s)

3: 75 percent / K₂CO₃ / methanol / 2 h / 20 °C

4: 85 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / various solvent(s) / 16 h / 90 °C

5: 54 percent / H₂ / Pd/C / ethanol / 16 h

6: 93 percent / aq. NaOH / tetrahydrofuran; methanol / 16 h

7: 69 percent / EDC; HOBT; NMM / dimethylformamide / 16 h / 20 °C

With 4-methyl-morpholine; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; di-isopropyl azodicarboxylate; hydrogen; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Mitsunobu reaction / 2: Sonogashira coupling / 4: Sonogashira coupling;

DOI:10.1021/jm049666k

upstream raw materials:

3S-3-amino-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid tert-butyl ester

2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-[2-(6-methylamino-pyridin-2-yl)-ethyl]-benzoic acid

methyl 4-iodosalicylate

2-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-4-iodo-benzoic acid methyl ester