N-<4-(4-hydroxyphenyl)butyryl>-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-N^ω-nitro-L-arginine methyl ester

Base Information

• Chemical Name: N-<4-(4-hydroxyphenyl)butyryl>-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-N^ω-nitro-L-arginine methyl ester
• CAS No.: 86778-75-8
• Molecular Formula: C₃₄H₄₇N₇O₁₀
• Molecular Weight: 713.788

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

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

There total 7 articles about N-<4-(4-hydroxyphenyl)butyryl>-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: 92.0%

nitro-L-arginine methyl ester hydrochloride (51298-62-5) + N-<4-(4-hydroxyphenyl)butyryl>-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanine (86778-74-7) → N-<4-(4-hydroxyphenyl)butyryl>-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-Nω-nitro-L-arginine methyl ester (86778-75-8)

Guidance literature:

With N-Ethylmaleimide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; for 48h; pH 7.0-7.5;

DOI:10.1021/jm00369a017

Reference yield:

4-(4-hydroxyphenyl)butanoic acid (7021-11-6) → N-<4-(4-hydroxyphenyl)butyryl>-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-Nω-nitro-L-arginine methyl ester (86778-75-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / HOBt, NEM, DCC / tetrahydrofuran; dimethylformamide / 17 h / 25 °C / pH 7.0-7.5

2: 100 percent / H₂ / 10percent Pd/C (wet with H₂O) / ethanol / 3 h / 3102.9 Torr

3: 100 percent / HOBt, NEM, DCC / tetrahydrofuran / 72 h / 25 °C / pH 7.0-7.5

4: 66 percent / 2.5 N NaOH / methanol / 25 °C

5: 92 percent / HOBt, NEM, DCC / tetrahydrofuran / 48 h / pH 7.0-7.5

With N-Ethylmaleimide; sodium hydroxide; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on carbon; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00369a017

Reference yield:

methyl 4-(4-hydroxyphenyl)butanoate (22320-10-1) → N-<4-(4-hydroxyphenyl)butyryl>-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-Nω-nitro-L-arginine methyl ester (86778-75-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 48percent HBr / acetic acid / Heating

2: 83 percent / HOBt, NEM, DCC / tetrahydrofuran; dimethylformamide / 17 h / 25 °C / pH 7.0-7.5

3: 100 percent / H₂ / 10percent Pd/C (wet with H₂O) / ethanol / 3 h / 3102.9 Torr

4: 100 percent / HOBt, NEM, DCC / tetrahydrofuran / 72 h / 25 °C / pH 7.0-7.5

5: 66 percent / 2.5 N NaOH / methanol / 25 °C

6: 92 percent / HOBt, NEM, DCC / tetrahydrofuran / 48 h / pH 7.0-7.5

With N-Ethylmaleimide; sodium hydroxide; hydrogen bromide; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on carbon; In tetrahydrofuran; methanol; ethanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm00369a017

upstream raw materials:

nitro-L-arginine methyl ester hydrochloride

N-<4-(4-hydroxyphenyl)butyryl>-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanine

4-(4-hydroxyphenyl)butanoic acid

methyl 4-(4-hydroxyphenyl)butanoate

Downstream raw materials:

N-<4-(4-hydroxyphenyl)butyryl>-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-N^ω-nitro-L-arginine

N-[4-(4-hydroxyphenyl)butyryl]-L-prolyl-DL-α-methyl-3,4-dimethoxyphenylalanyl-L-arginine

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