{[2-({(S)-2-[(S)-2-{[(S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionylamino]-propionyl}-methyl-amino)-acetyl]-methyl-amino}-acetic acid pentafluorophenyl ester

Base Information

• Chemical Name: {[2-({(S)-2-[(S)-2-{[(S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionylamino]-propionyl}-methyl-amino)-acetyl]-methyl-amino}-acetic acid pentafluorophenyl ester
• CAS No.: 112196-55-1
• Molecular Formula: C₃₇H₄₇F₅N₆O₁₀
• Molecular Weight: 830.806
• Mol file: 112196-55-1.mol

Synonyms:{[2-({(S)-2-[(S)-2-{[(S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionylamino]-propionyl}-methyl-amino)-acetyl]-methyl-amino}-acetic acid pentafluorophenyl ester

Chemical Property of {[2-({(S)-2-[(S)-2-{[(S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionylamino]-propionyl}-methyl-amino)-acetyl]-methyl-amino}-acetic acid pentafluorophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {[2-({(S)-2-[(S)-2-{[(S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionylamino]-propionyl}-methyl-amino)-acetyl]-methyl-amino}-acetic acid pentafluorophenyl ester

There total 12 articles about {[2-({(S)-2-[(S)-2-{[(S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionylamino]-propionyl}-methyl-amino)-acetyl]-methyl-amino}-acetic acid pentafluorophenyl 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: 65.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + Boc-D-Ala-Ala-N-Me-Tyr(OMe)-Ala-N-Me-Gly-N-Me-Gly-OH (112219-52-0) → {[2-({(S)-2-[(S)-2-{[(S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionylamino]-propionyl}-methyl-amino)-acetyl]-methyl-amino}-acetic acid pentafluorophenyl ester (112196-55-1)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 25 ℃; for 24h;

DOI:10.1021/jo00238a005

Reference yield:

Boc-(R)-Ala (3744-87-4,7764-95-6,15761-38-3) → {[2-({(S)-2-[(S)-2-{[(S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionylamino]-propionyl}-methyl-amino)-acetyl]-methyl-amino}-acetic acid pentafluorophenyl ester (112196-55-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 36 h / 25 °C

2: 78 percent / LiOH / tetrahydrofuran; methanol; H₂O / 3 h / 25 °C

3: 71 percent / dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBT) / CH₂Cl₂ / 36 h / 0 °C

4: 82 percent / LiOH / tetrahydrofuran; methanol; H₂O / 3 h / 25 °C

5: 64 percent / dicyclohexylcarbodiimine (DCC), 1-hydroxybenzotrazole (HOBT) / CH₂Cl₂ / 24 h / 25 °C

6: 86 percent / LiOH / tetrahydrofuran; methanol; H₂O / 3 h / 25 °C

7: 65 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDCI) / CH₂Cl₂ / 24 h / 25 °C

With lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo00238a005

Reference yield:

methyl 2-[[2-[tert-butoxycarbonyl(methyl)amino]acetyl]methylamino]acetate (42492-58-0) → {[2-({(S)-2-[(S)-2-{[(S)-2-((R)-2-tert-Butoxycarbonylamino-propionylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionylamino]-propionyl}-methyl-amino)-acetyl]-methyl-amino}-acetic acid pentafluorophenyl ester (112196-55-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / CF₃CO₂H / CH₂Cl₂ / 0.5 h / 25 °C

2: 64 percent / dicyclohexylcarbodiimine (DCC), 1-hydroxybenzotrazole (HOBT) / CH₂Cl₂ / 24 h / 25 °C

3: 86 percent / LiOH / tetrahydrofuran; methanol; H₂O / 3 h / 25 °C

4: 65 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDCI) / CH₂Cl₂ / 24 h / 25 °C

With lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo00238a005

upstream raw materials:

2,3,4,5,6-pentafluorophenol

Boc-D-Ala-Ala-N-Me-Tyr(OMe)-Ala-N-Me-Gly-N-Me-Gly-OH

Boc-(R)-Ala

methyl 2-[[2-[tert-butoxycarbonyl(methyl)amino]acetyl]methylamino]acetate

Downstream raw materials:

Cyclo-(D-Ala-Ala-N-Me-Tyr(OCH₃)-Ala-N-Me-Gly-N-Me-Gly)