N-(3-phenylpropanoyl)-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-L-arginine methyl ester

Base Information

• Chemical Name: N-(3-phenylpropanoyl)-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-L-arginine methyl ester
• CAS No.: 88105-86-6
• Molecular Formula: C₃₁H₄₁N₇O₇
• Molecular Weight: 623.709

Synonyms:N-(3-phenylpropanoyl)-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-L-arginine methyl ester

Chemical Property of N-(3-phenylpropanoyl)-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-L-arginine methyl ester

Chemical Property:

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Technology Process of N-(3-phenylpropanoyl)-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-L-arginine methyl ester

There total 7 articles about N-(3-phenylpropanoyl)-L-prolyl-DL-α-methylphenylalanyl-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: 39.0%

N-(1'-oxo-3'-phenylpropyl)pyrrolidine-2-carboxylic acid (73030-06-5) + DL-α-methylphenylalanyl-Nω-nitro-L-arginine methyl ester (88084-20-2) → N-(3-phenylpropanoyl)-L-prolyl-DL-α-methylphenylalanyl-Nω-nitro-L-arginine methyl ester (88105-86-6)

Guidance literature:

With N-Ethylmaleimide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; for 72h; pH 7.0-7.5;

DOI:10.1021/jm00369a017

Reference yield:

(S)-1-(3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid benzyl ester (88105-74-2) → N-(3-phenylpropanoyl)-L-prolyl-DL-α-methylphenylalanyl-Nω-nitro-L-arginine methyl ester (88105-86-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / H₂ / 10percent Pd/C / ethanol / 3102.9 Torr

2: 39 percent / HOBt, NEM, DCC / tetrahydrofuran / 72 h / pH 7.0-7.5

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

DOI:10.1021/jm00369a017

Reference yield:

hydrocinnamic acid chloride (645-45-4) → N-(3-phenylpropanoyl)-L-prolyl-DL-α-methylphenylalanyl-Nω-nitro-L-arginine methyl ester (88105-86-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / pyridine / CH₂Cl₂ / 3 h / 25 °C

2: 95 percent / H₂ / 10percent Pd/C / ethanol / 3102.9 Torr

3: 39 percent / HOBt, NEM, DCC / tetrahydrofuran / 72 h / pH 7.0-7.5

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

DOI:10.1021/jm00369a017

upstream raw materials:

N-(1'-oxo-3'-phenylpropyl)pyrrolidine-2-carboxylic acid

DL-α-methylphenylalanyl-N^ω-nitro-L-arginine methyl ester

2-methyl-3-phenylalanine

(+/-)-N-(tert-butoxycarbonyl)-α-methylphenylalanine

Downstream raw materials:

N-(3-phenylpropanoyl)-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-L-arginine

N-(3-phenylpropanoyl)-L-prolyl-DL-α-methylphenylalanyl-L-arginine

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