N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-N²-tert-butyloxycarbonyl-L-ornithinamide

Base Information

• Chemical Name: N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-N²-tert-butyloxycarbonyl-L-ornithinamide
• CAS No.: 444154-92-1
• Molecular Formula: C₃₀H₄₀N₄O₇
• Molecular Weight: 568.67

Synonyms:N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-N²-tert-butyloxycarbonyl-L-ornithinamide

Chemical Property of N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-N²-tert-butyloxycarbonyl-L-ornithinamide

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-N²-tert-butyloxycarbonyl-L-ornithinamide

There total 4 articles about N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-N²-tert-butyloxycarbonyl-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: 94.0%

Boc-Orn(Z)-OH (2480-93-5) + (S)-3-amino-1-benzyloxypiperidin-2-one hydrobromide → N5-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-N2-tert-butyloxycarbonyl-L-ornithinamide (444154-92-1)

Guidance literature:

With dmap; 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃;

DOI:10.1021/jo0256078

Reference yield:

benzyl bromide (100-39-0) → N5-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-N2-tert-butyloxycarbonyl-L-ornithinamide (444154-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NH₂OH*HCl / methanol / 0.33 h / Heating

1.2: Et₃N; 3 Angstroem molecular sieves / methanol / 1 h / Heating

1.3: 65 percent / K₂CO₃ / dimethylformamide / 20 °C

2.1: 92 percent / HBr; AcOH / CH₂Cl₂ / 1 h / 20 °C

3.1: 94 percent / HOAt; EDC; DMAP / CH₂Cl₂ / 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; hydroxylamine hydrochloride; hydrogen bromide; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol; dichloromethane;

DOI:10.1021/jo0256078

Reference yield:

(S)-3-benzyloxycarbonylamino-1-benzyloxypiperidin-2-one (125050-20-6) → N5-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-N2-tert-butyloxycarbonyl-L-ornithinamide (444154-92-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / HBr; AcOH / CH₂Cl₂ / 1 h / 20 °C

2: 94 percent / HOAt; EDC; DMAP / CH₂Cl₂ / 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; hydrogen bromide; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1021/jo0256078

upstream raw materials:

Boc-Orn(Z)-OH

benzyl bromide

(S)-3-benzyloxycarbonylamino-1-benzyloxypiperidin-2-one

Downstream raw materials:

N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide

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

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

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

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