N,N'-bis-tert-butoxycarbonyl-4-guanidinomethyl-benzoic acid

Base Information

• Chemical Name: N,N'-bis-tert-butoxycarbonyl-4-guanidinomethyl-benzoic acid
• CAS No.: 246224-53-3
• Molecular Formula: C₁₉H₂₇N₃O₆
• Molecular Weight: 393.44
• Mol file: 246224-53-3.mol

Synonyms:N,N'-bis-tert-butoxycarbonyl-4-guanidinomethyl-benzoic acid

Chemical Property of N,N'-bis-tert-butoxycarbonyl-4-guanidinomethyl-benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of N,N'-bis-tert-butoxycarbonyl-4-guanidinomethyl-benzoic acid

There total 1 articles about N,N'-bis-tert-butoxycarbonyl-4-guanidinomethyl-benzoic acid 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: 95.0%

p-aminomethylbenzoic acid (56-91-7) + N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-54-2,862686-58-6,1143572-00-2) → N,N'-bis-tert-butoxycarbonyl-4-guanidinomethyl-benzoic acid (246224-53-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; Heating;

DOI:10.1016/j.bmcl.2007.01.004

Reference yield: 49.0%

N,N'-bis-tert-butoxycarbonyl-4-guanidinomethyl-benzoic acid (246224-53-3) → 2(S)-[2(S)-(4-guanidinomethyl-benzoylamino)-3-methyl-butyrylamino]-3-phenyl-propionic acid (936571-73-2)

Guidance literature:

N,N'-bis-tert-butoxycarbonyl-4-guanidinomethyl-benzoic acid; H-Val-Phe-Wang resin; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

With chlorotriisopropylsilane; methyl-phenyl-thioether; trifluoroacetic acid; In water; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2007.01.004

Reference yield:

N,N'-bis-tert-butoxycarbonyl-4-guanidinomethyl-benzoic acid (246224-53-3) → N-[1(S)-(1(S)-benzylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-methyl-propyl]-4-guanidinomethyl-benzamide

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N'-diisopropylcarbodiimide; HBTU / dimethylformamide / 0.25 h / 20 °C

1.2: 49 percent / trifluoroacetic acid; triisopropylsilane; thioanisole / H₂O / 12 h / 20 °C

2.1: HATU; N,N'-diisopropylethylamine / dimethylformamide / 0.02 h / 20 °C

2.2: 45 percent / dimethylformamide / 20 h / 20 °C

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; diisopropyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2007.01.004

upstream raw materials:

p-aminomethylbenzoic acid

N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine

Downstream raw materials:

2(S)-[2(S)-(4-guanidinomethyl-benzoylamino)-3-methyl-butyrylamino]-3-phenyl-propionic acid