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

Base Information

• Chemical Name: 3-{4-[2-(6-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethylamino}-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid
• CAS No.: 801239-56-5
• Molecular Formula: C₃₈H₅₃N₅O₉S
• Molecular Weight: 755.933
• Mol file: 801239-56-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 3-{4-[2-(6-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethylamino}-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid 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%

3S-3-amino-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid tert-butyl ester (185563-98-8) + 4-[2-(6-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethylamino}-pyridin-2-yl)-ethyl]-benzoic acid (801239-97-4) → 3-{4-[2-(6-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethylamino}-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid (801239-56-5)

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:

2-Amino-6-bromopyridine (19798-81-3,1184170-10-2) → 3-{4-[2-(6-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethylamino}-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid (801239-56-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 65 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / various solvent(s) / 16 h / 90 °C

2: H₂ / Pd/C / ethanol / 16 h

3: aq. NaOH / methanol; tetrahydrofuran / 16 h

4: 3 A molecular sieves / CH₂Cl₂; dimethylformamide / 4 h / 20 °C

5: 120 mg / NaCNBH₃; 3 A molecular sieves / CH₂Cl₂; dimethylformamide / 16 h / 0 - 20 °C

6: 78 percent / EDC; HOBT; NMM / dimethylformamide / 16 h / 20 °C

With 4-methyl-morpholine; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; 3 A molecular sieve; hydrogen; sodium cyanoborohydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Sonogashira coupling;

DOI:10.1021/jm049666k

Reference yield:

ethyl 4-ethynylbenzoate (10602-03-6) → 3-{4-[2-(6-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethylamino}-pyridin-2-yl)-ethyl]-benzoylamino}-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid (801239-56-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 65 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / various solvent(s) / 16 h / 90 °C

2: H₂ / Pd/C / ethanol / 16 h

3: aq. NaOH / methanol; tetrahydrofuran / 16 h

4: 3 A molecular sieves / CH₂Cl₂; dimethylformamide / 4 h / 20 °C

5: 120 mg / NaCNBH₃; 3 A molecular sieves / CH₂Cl₂; dimethylformamide / 16 h / 0 - 20 °C

6: 78 percent / EDC; HOBT; NMM / dimethylformamide / 16 h / 20 °C

With 4-methyl-morpholine; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; 3 A molecular sieve; hydrogen; sodium cyanoborohydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Sonogashira coupling;

DOI:10.1021/jm049666k

upstream raw materials:

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

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

2-Amino-6-bromopyridine

ethyl 4-ethynylbenzoate