cyclo(glycyl-phenylalanyl-prolyl-N(beta)-(N-maleoylglycyl)-alpha,beta-diaminopropanoyl)

Base Information

• Chemical Name: cyclo(glycyl-phenylalanyl-prolyl-N(beta)-(N-maleoylglycyl)-alpha,beta-diaminopropanoyl)
• CAS No.: 77087-68-4
• Molecular Formula: C25H28 N6 O7
• Molecular Weight: 524.53
• Mol file: 77087-68-4.mol

Synonyms:Cyclic[3-[[(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)acetyl]amino]-L-alanylglycyl-L-phenylalanyl-D-prolyl];Pyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine, cyclic peptide deriv.

Chemical Property of cyclo(glycyl-phenylalanyl-prolyl-N(beta)-(N-maleoylglycyl)-alpha,beta-diaminopropanoyl)

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 968.8°C at 760 mmHg
• Flash Point: 539.7°C
• PSA: 174.09000
• Density: 1.425g/cm³
• LogP: -1.38620

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of cyclo(glycyl-phenylalanyl-prolyl-N(beta)-(N-maleoylglycyl)-alpha,beta-diaminopropanoyl)

There total 5 articles about cyclo(glycyl-phenylalanyl-prolyl-N(beta)-(N-maleoylglycyl)-alpha,beta-diaminopropanoyl) 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:

(S)-2-({(R)-1-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-tert-butoxycarbonylamino-propionic acid → cyclo(glycyl-L-phenylalanyl-D-prolyl-Nβ-(N-maleoylglycyl)-L-α,β-diaminopropanoyl) (77087-68-4)

Guidance literature:

Multi-step reaction with 5 steps

1: DCC, pyridine / 1.) 4 deg C, 20 h, 2.) 25 deg C, 1 h

2: 84 percent / acetic acid, H₂ / 10percent Pd/C / methanol / 3 h / 0 °C / 760 Torr

3: 14.5 percent / pyridine / dimethylformamide / 8 h / 90 °C

4: 4 N HCl / dioxane / 0.5 h / 25 °C

5: TEA, DCC, HOBt / dimethylformamide / 1.) 6 deg C, 10 h, 2.) 25 deg C, 1 h

With pyridine; hydrogenchloride; TEA; hydrogen; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00137a017

Reference yield:

methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-Nβ-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate (77087-64-0) → cyclo(glycyl-L-phenylalanyl-D-prolyl-Nβ-(N-maleoylglycyl)-L-α,β-diaminopropanoyl) (77087-68-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1 N KOH / ethanol; H₂O / 0.17 h

2: DCC, pyridine / 1.) 4 deg C, 20 h, 2.) 25 deg C, 1 h

3: 84 percent / acetic acid, H₂ / 10percent Pd/C / methanol / 3 h / 0 °C / 760 Torr

4: 14.5 percent / pyridine / dimethylformamide / 8 h / 90 °C

5: 4 N HCl / dioxane / 0.5 h / 25 °C

6: TEA, DCC, HOBt / dimethylformamide / 1.) 6 deg C, 10 h, 2.) 25 deg C, 1 h

With pyridine; hydrogenchloride; potassium hydroxide; TEA; hydrogen; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00137a017

Reference yield:

(S)-2-({(R)-1-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-tert-butoxycarbonylamino-propionic acid 2,4,5-trichloro-phenyl ester (77087-65-1) → cyclo(glycyl-L-phenylalanyl-D-prolyl-Nβ-(N-maleoylglycyl)-L-α,β-diaminopropanoyl) (77087-68-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / acetic acid, H₂ / 10percent Pd/C / methanol / 3 h / 0 °C / 760 Torr

2: 14.5 percent / pyridine / dimethylformamide / 8 h / 90 °C

3: 4 N HCl / dioxane / 0.5 h / 25 °C

4: TEA, DCC, HOBt / dimethylformamide / 1.) 6 deg C, 10 h, 2.) 25 deg C, 1 h

With pyridine; hydrogenchloride; TEA; hydrogen; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00137a017

upstream raw materials:

cyclo(glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoyl)

(S)-2-({(R)-1-[(S)-2-(2-Amino-acetylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-tert-butoxycarbonylamino-propionic acid 2,4,5-trichloro-phenyl ester

methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate

(S)-2-({(R)-1-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-tert-butoxycarbonylamino-propionic acid 2,4,5-trichloro-phenyl ester

Refernces