N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N⁵-hydroxy-N²-methyl-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide

Base Information

• Chemical Name: N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N⁵-hydroxy-N²-methyl-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide
• CAS No.: 444154-90-9
• Molecular Formula: C₄₃H₆₂N₈O₁₃
• Molecular Weight: 899.011

Synonyms:N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N⁵-hydroxy-N²-methyl-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide

Chemical Property of N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N⁵-hydroxy-N²-methyl-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide

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Technology Process of N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N⁵-hydroxy-N²-methyl-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide

There total 4 articles about N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N⁵-hydroxy-N²-methyl-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide 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: 31.0%

3-(3-(tert-butoxycarbonylamino)propanamido)propanoic acid (126074-82-6) + {(S)-1-[(S)-4-Benzyloxycarbonylamino-1-((S)-1-hydroxy-2-oxo-piperidin-3-ylcarbamoyl)-butylcarbamoyl]-4-hydroxyamino-butyl}-methyl-carbamic acid benzyl ester; hydrochloride → N5-benzyloxycarbonyl-(N2-benzyloxycarbonyl-N5-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N5-hydroxy-N2-methyl-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide (444154-90-9)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jo0256078

Reference yield:

N2-benzyloxycarbonyl-N2-methyl-N5-phenylmethylene-N5-oxide-L-ornithine (444154-65-8) → N5-benzyloxycarbonyl-(N2-benzyloxycarbonyl-N5-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N5-hydroxy-N2-methyl-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide (444154-90-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.949 g / HOAt; EDC; DMAP / dimethylformamide / 0 - 20 °C

2: 75 percent / NH₂OH*HCl / methanol / 0.33 h / 60 - 70 °C

3: 31 percent / BOP; (i-Pr)2NEt / dimethylformamide / 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; hydroxylamine hydrochloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo0256078

Reference yield:

C20H22N2O5 → N5-benzyloxycarbonyl-(N2-benzyloxycarbonyl-N5-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N5-hydroxy-N2-methyl-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide (444154-90-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / NaH / tetrahydrofuran / 24 h / 20 °C

2: 0.949 g / HOAt; EDC; DMAP / dimethylformamide / 0 - 20 °C

3: 75 percent / NH₂OH*HCl / methanol / 0.33 h / 60 - 70 °C

4: 31 percent / BOP; (i-Pr)2NEt / dimethylformamide / 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; hydroxylamine hydrochloride; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo0256078

upstream raw materials:

3-(3-(tert-butoxycarbonylamino)propanamido)propanoic acid

N²-benzyloxycarbonyl-N²-methyl-N⁵-phenylmethylene-N⁵-oxide-L-ornithine

N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N²-methyl-N⁵-phenylmethylene-N⁵-oxide-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide

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