N-(4-phenylbutyryl)-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-N^ω-nitro-L-arginine methyl ester

Base Information

• Chemical Name: N-(4-phenylbutyryl)-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-N^ω-nitro-L-arginine methyl ester
• CAS No.: 88105-91-3
• Molecular Formula: C₃₄H₄₇N₇O₉
• Molecular Weight: 697.789

Synonyms:N-(4-phenylbutyryl)-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-N^ω-nitro-L-arginine methyl ester

Chemical Property of N-(4-phenylbutyryl)-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-N^ω-nitro-L-arginine methyl ester

Chemical Property:

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Technology Process of N-(4-phenylbutyryl)-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-N^ω-nitro-L-arginine methyl ester

There total 6 articles about N-(4-phenylbutyryl)-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-N^ω-nitro-L-arginine methyl 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: 55.0%

nitro-L-arginine methyl ester hydrochloride (51298-62-5) + N-(4-phenylbutyryl)-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanine (86778-87-2) → N-(4-phenylbutyryl)-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-Nω-nitro-L-arginine methyl ester (88105-91-3)

Guidance literature:

With N-Ethylmaleimide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; pH 7.0-7.5;

DOI:10.1021/jm00369a017

Reference yield:

phenylbutyric acid chloride (18496-54-3) → N-(4-phenylbutyryl)-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-Nω-nitro-L-arginine methyl ester (88105-91-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / pyridine / CH₂Cl₂ / 3 h / 25 °C

2: 79 percent / H₂ / 10percent Pd/C / ethanol / 3102.9 Torr

3: 98 percent / HOBt, NEM, DCC / tetrahydrofuran / 72 h / 25 °C / pH 7.0-7.5

4: 93 percent / 2.5 N NaOH / methanol / 25 °C

5: 55 percent / HOBt, NEM, DCC / tetrahydrofuran / pH 7.0-7.5

With pyridine; N-Ethylmaleimide; sodium hydroxide; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1021/jm00369a017

Reference yield:

N-(4-phenylbutyryl)-L-proline benzyl ester (88105-73-1) → N-(4-phenylbutyryl)-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-Nω-nitro-L-arginine methyl ester (88105-91-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / H₂ / 10percent Pd/C / ethanol / 3102.9 Torr

2: 98 percent / HOBt, NEM, DCC / tetrahydrofuran / 72 h / 25 °C / pH 7.0-7.5

3: 93 percent / 2.5 N NaOH / methanol / 25 °C

4: 55 percent / HOBt, NEM, DCC / tetrahydrofuran / pH 7.0-7.5

With N-Ethylmaleimide; sodium hydroxide; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol;

DOI:10.1021/jm00369a017

upstream raw materials:

nitro-L-arginine methyl ester hydrochloride

N-(4-phenylbutyryl)-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanine

phenylbutyric acid chloride

N-(4-phenylbutanoyl)-L-proline

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