N¹-Ethyl-N¹-(N-tert-butyloxycarbonyl-L-tyrosyl-D-arginylglycyl)-L-4-nitrophenylalaninamide

Base Information

• Chemical Name: N¹-Ethyl-N¹-(N-tert-butyloxycarbonyl-L-tyrosyl-D-arginylglycyl)-L-4-nitrophenylalaninamide
• CAS No.: 96154-71-1
• Molecular Formula: C₃₃H₄₇N₉O₉
• Molecular Weight: 713.791

Synonyms:N¹-Ethyl-N¹-(N-tert-butyloxycarbonyl-L-tyrosyl-D-arginylglycyl)-L-4-nitrophenylalaninamide

Chemical Property of N¹-Ethyl-N¹-(N-tert-butyloxycarbonyl-L-tyrosyl-D-arginylglycyl)-L-4-nitrophenylalaninamide

Chemical Property:

Purity/Quality:

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Technology Process of N¹-Ethyl-N¹-(N-tert-butyloxycarbonyl-L-tyrosyl-D-arginylglycyl)-L-4-nitrophenylalaninamide

There total 6 articles about N¹-Ethyl-N¹-(N-tert-butyloxycarbonyl-L-tyrosyl-D-arginylglycyl)-L-4-nitrophenylalaninamide 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: 81.0%

N1-ethyl-N1-glycyl-L-4-nitrophenylalaninamide hydrochloride + N-(tert-butyloxycarbonyl)-L-tyrosyl-D-arginine hydrochloride (88331-11-7) → N1-Ethyl-N1-(N-tert-butyloxycarbonyl-L-tyrosyl-D-arginylglycyl)-L-4-nitrophenylalaninamide (96154-71-1)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 5 ℃; for 48h;

DOI:10.1021/jm00125a028

Reference yield:

Boc-Phe(p-NO2)-OH (33305-77-0) → N1-Ethyl-N1-(N-tert-butyloxycarbonyl-L-tyrosyl-D-arginylglycyl)-L-4-nitrophenylalaninamide (96154-71-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) isobutyl chloroformate, N-methylmorpholine, 2) NH₃(gas) / 1) DMF, -15 deg C, 5 min, 2) -15 deg C, 1 h

2: 97 percent / 2 M HCl, HOAc, anisole / 0.5 h / Ambient temperature

3: 55 percent / NaHCO₃ / ethanol / 6.5 h / Heating

4: 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / 24 h / Ambient temperature

5: 2 M HCl, HOAc, anisole / 0.75 h / Ambient temperature

6: 81 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide, N-methylmorpholine / dimethylformamide / 48 h / 5 °C

With 4-methyl-morpholine; hydrogenchloride; ammonia; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; methoxybenzene; dicyclohexyl-carbodiimide; isobutyl chloroformate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00125a028

Reference yield:

N1-Ethyl-L-4-nitrophenylalaninamide (96154-68-6) → N1-Ethyl-N1-(N-tert-butyloxycarbonyl-L-tyrosyl-D-arginylglycyl)-L-4-nitrophenylalaninamide (96154-71-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / 24 h / Ambient temperature

2: 2 M HCl, HOAc, anisole / 0.75 h / Ambient temperature

3: 81 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide, N-methylmorpholine / dimethylformamide / 48 h / 5 °C

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; acetic acid; methoxybenzene; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1021/jm00125a028

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-tyrosyl-D-arginine hydrochloride

Boc-Phe(p-NO₂)-OH

N¹-Ethyl-L-4-nitrophenylalaninamide

N¹--N¹-ethyl-L-4-nitrophenylalaninamide

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