1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: 1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester
• CAS No.: 259867-09-9
• Molecular Formula: C₅₇H₇₀N₈O₁₂
• Molecular Weight: 1059.23

Synonyms:

Chemical Property of 1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester

There total 10 articles about 1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl 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:

4-bromo-phenol (106-41-2) → 1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester (259867-09-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Na / diethyl ether

1.2: 74 percent / ZnBr₂ / CH₂Cl₂

2.1: 93 percent / K₂CO₃ / acetone / Heating

3.1: 85 percent / t-BuLi / tetrahydrofuran / -78 °C

4.1: BuLi / tetrahydrofuran / -78 - -20 °C

5.1: 56 percent / TFA / H₂O

6.1: H₂ / Pd/C / methanol

7.1: HOBt; EDCI; DIPEA / CH₂Cl₂

8.1: LiOH / acetonitrile

9.1: HOBt; EDCI; DIPEA / TFA / CH₂Cl₂

With lithium hydroxide; n-butyllithium; hydrogen; tert.-butyl lithium; sodium; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile; 1.1: Metallation / 1.2: Alkylation / 2.1: Methylation / 3.1: Carbonylation / 4.1: Addition / 5.1: Hydrolysis / 6.1: Hydrogenation / 7.1: Acylation / 8.1: Hydrolysis / 9.1: Acylation;

DOI:10.1016/S0040-4039(99)01930-9

Reference yield:

4-Methoxy-3-(γ,γ-dimethylallyl)benzaldehyde (56074-98-7) → 1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester (259867-09-9)

Guidance literature:

Multi-step reaction with 6 steps

1: BuLi / tetrahydrofuran / -78 - -20 °C

2: 56 percent / TFA / H₂O

3: H₂ / Pd/C / methanol

4: HOBt; EDCI; DIPEA / CH₂Cl₂

5: LiOH / acetonitrile

6: HOBt; EDCI; DIPEA / TFA / CH₂Cl₂

With lithium hydroxide; n-butyllithium; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1: Addition / 2: Hydrolysis / 3: Hydrogenation / 4: Acylation / 5: Hydrolysis / 6: Acylation;

DOI:10.1016/S0040-4039(99)01930-9

Reference yield:

4-bromo-2-(3-methylbut-2-en-1-yl)phenol (151071-00-0) → 1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester (259867-09-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 93 percent / K₂CO₃ / acetone / Heating

2: 85 percent / t-BuLi / tetrahydrofuran / -78 °C

3: BuLi / tetrahydrofuran / -78 - -20 °C

4: 56 percent / TFA / H₂O

5: H₂ / Pd/C / methanol

6: HOBt; EDCI; DIPEA / CH₂Cl₂

7: LiOH / acetonitrile

8: HOBt; EDCI; DIPEA / TFA / CH₂Cl₂

With lithium hydroxide; n-butyllithium; hydrogen; tert.-butyl lithium; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; 1: Methylation / 2: Carbonylation / 3: Addition / 4: Hydrolysis / 5: Hydrogenation / 6: Acylation / 7: Hydrolysis / 8: Acylation;

DOI:10.1016/S0040-4039(99)01930-9

upstream raw materials:

4-bromo-phenol

4-Methoxy-3-(γ,γ-dimethylallyl)benzaldehyde

4-bromo-2-(3-methylbut-2-en-1-yl)phenol

prenyl bromide

Downstream raw materials:

cyclic Pro-Gly-Val-Gly-Tyr(β-OH,4-methyl,3-(2-methylbutyl))-Gly-Trp

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