5-acetylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonyl-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester

Base Information

• Chemical Name: 5-acetylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonyl-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester
• CAS No.: 849599-74-2
• Molecular Formula: C₅₂H₆₆N₁₀O₁₁
• Molecular Weight: 1007.16

Synonyms:5-acetylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonyl-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester

Chemical Property of 5-acetylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonyl-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester

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Technology Process of 5-acetylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonyl-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester

There total 10 articles about 5-acetylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonyl-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine 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: 57.0%

Nε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester (849599-59-3) + 5-{[5-acetylamino-2-(4-methoxybenzyl)-2H-pyrazole-3-carbonyl]-amino}-2-(4-methoxybenzyl)-2H-pyrazole-3-carboxylic acid (849599-57-1) → 5-acetylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonyl-Nε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester (849599-74-2)

Guidance literature:

With 2-chloro-1-methyl-pyridinium iodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at 20 ℃;

DOI:10.1021/ja045558b

Reference yield:

t-Boc-L-valine (13734-41-3) → 5-acetylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonyl-Nε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester (849599-74-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: HCTU; Cl-HOBt; 2,6-lutidine / CH₂Cl₂; dimethylformamide / 0.17 h / 0 °C

1.2: 97 percent / 2,6-lutidine / CH₂Cl₂; dimethylformamide

2.1: CF₃CO₂H / CH₂Cl₂ / 0 °C

3.1: HCTU; Cl-HOBt; 2,6-lutidine / CH₂Cl₂; dimethylformamide / 0.17 h / 0 °C

3.2: 75 percent / CH₂Cl₂; dimethylformamide

4.1: 100 percent / H₂ / Pd/C / methanol

5.1: 57 percent / 2-chloro-1-methylpyridinium iodide; diisopropylethylamine / CH₂Cl₂; tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); 2-chloro-1-methyl-pyridinium iodide; hydrogen; N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja045558b

Reference yield:

L-valyl-L-phenylalanine methyl ester (39614-17-0,128557-46-0,145313-30-0) → 5-acetylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonyl-Nε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester (849599-74-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HCTU; Cl-HOBt; 2,6-lutidine / CH₂Cl₂; dimethylformamide / 0.17 h / 0 °C

1.2: 75 percent / CH₂Cl₂; dimethylformamide

2.1: 100 percent / H₂ / Pd/C / methanol

3.1: 57 percent / 2-chloro-1-methylpyridinium iodide; diisopropylethylamine / CH₂Cl₂; tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); 2-chloro-1-methyl-pyridinium iodide; hydrogen; N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja045558b

upstream raw materials:

N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester

5-{[5-acetylamino-2-(4-methoxybenzyl)-2H-pyrazole-3-carbonyl]-amino}-2-(4-methoxybenzyl)-2H-pyrazole-3-carboxylic acid

t-Boc-L-valine

L-valyl-L-phenylalanine methyl ester

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