N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-(benzyloxycarbonyl)amino}methyl)-2-pyridylcarbonyl]-N-[2-(benzyloxycarbonylamino)ethyl]-L-histidinamide

Base Information

• Chemical Name: N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-(benzyloxycarbonyl)amino}methyl)-2-pyridylcarbonyl]-N-[2-(benzyloxycarbonylamino)ethyl]-L-histidinamide
• CAS No.: 209467-33-4
• Molecular Formula: C₄₁H₄₄N₈O₈
• Molecular Weight: 776.849

Synonyms:

Chemical Property of N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-(benzyloxycarbonyl)amino}methyl)-2-pyridylcarbonyl]-N-[2-(benzyloxycarbonylamino)ethyl]-L-histidinamide

Chemical Property:

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Technology Process of N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-(benzyloxycarbonyl)amino}methyl)-2-pyridylcarbonyl]-N-[2-(benzyloxycarbonylamino)ethyl]-L-histidinamide

There total 7 articles about N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-(benzyloxycarbonyl)amino}methyl)-2-pyridylcarbonyl]-N-[2-(benzyloxycarbonylamino)ethyl]-L-histidinamide 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:

2-benzyloxycarbonylaminoethylamine (72080-83-2) + 2-[(6-{[benzyloxycarbonyl-(2-benzyloxycarbonylamino-ethyl)-amino]-methyl}-pyridine-2-carbonyl)-amino]-3-(1H-imidazol-4-yl)-propionic acid (119802-78-7) → Nα-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-(benzyloxycarbonyl)amino}methyl)-2-pyridylcarbonyl]-N-[2-(benzyloxycarbonylamino)ethyl]-L-histidinamide (209467-33-4)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 51h;

DOI:10.1246/bcsj.71.1159

Reference yield:

2-benzyloxycarbonylaminoethylamine (72080-83-2) → Nα-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-(benzyloxycarbonyl)amino}methyl)-2-pyridylcarbonyl]-N-[2-(benzyloxycarbonylamino)ethyl]-L-histidinamide (209467-33-4)

Guidance literature:

Multi-step reaction with 7 steps

1: molecular sieve (4 Angstroem) / acetonitrile / 20 °C

2: NaBH₄ / methanol / 2 h / 20 °C

3: 4.86 g / aq. NaOH / CH₂Cl₂ / 3 h / 20 °C

4: aq. LiOH / tetrahydrofuran / 2 h / 0 °C

5: 615 mg / diphenylphosphoryl azide; Et₃N / dimethylformamide / 75 h / 0 - 20 °C

6: aq. LiOH / tetrahydrofuran / 2 h / 0 °C

7: 233 mg / diphenylphosphoryl azide; Et₃N / dimethylformamide / 51 h / 0 - 20 °C

With lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; 4 A molecular sieve; diphenylphosphoranyl azide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Reduction / 3: Acylation / 4: Hydrolysis / 5: Condensation / 6: Hydrolysis / 7: Condensation;

DOI:10.1246/bcsj.71.1159

Reference yield:

6-{[Benzyloxycarbonyl-(2-benzyloxycarbonylamino-ethyl)-amino]-methyl}-pyridine-2-carboxylic acid → Nα-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-(benzyloxycarbonyl)amino}methyl)-2-pyridylcarbonyl]-N-[2-(benzyloxycarbonylamino)ethyl]-L-histidinamide (209467-33-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 615 mg / diphenylphosphoryl azide; Et₃N / dimethylformamide / 75 h / 0 - 20 °C

2: aq. LiOH / tetrahydrofuran / 2 h / 0 °C

3: 233 mg / diphenylphosphoryl azide; Et₃N / dimethylformamide / 51 h / 0 - 20 °C

With lithium hydroxide; diphenylphosphoranyl azide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrolysis / 3: Condensation;

DOI:10.1246/bcsj.71.1159

upstream raw materials:

2-benzyloxycarbonylaminoethylamine

2-[(6-{[benzyloxycarbonyl-(2-benzyloxycarbonylamino-ethyl)-amino]-methyl}-pyridine-2-carbonyl)-amino]-3-(1H-imidazol-4-yl)-propionic acid

methyl 6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-benzyloxycarbonylamino}methyl)pyridine-2-carboxylate

methyl N^α-[6-({N-[2-(benzyloxycarbonylamino)ethyl]-N-benzyloxycarbonylamino}methyl)-2-pyridylcarbonyl]-L-histidinate

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