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

Base Information

Chemical Name:N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide
CAS No.:444154-93-2
Molecular Formula:C₂₅H₃₂N₄O₅
Molecular Weight:468.553
Hs Code.:

N<sup>5</sup>-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide

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

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

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

There total 6 articles about N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-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: 92.0%

: 444154-92-1
N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-N²-tert-butyloxycarbonyl-L-ornithinamide

: 444154-93-2
N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.666667h;
DOI:10.1021/jo0256078

Reference yield:

: 2480-93-5
Boc-Orn(Z)-OH

: 444154-93-2
N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / HOAt; EDC; DMAP / CH₂Cl₂ / 20 °C

2: 92 percent / TFA / CH₂Cl₂ / 0.67 h / 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jo0256078

Reference yield:

: 100-39-0
benzyl bromide

: 444154-93-2
N⁵-benzyloxycarbonyl-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide

Guidance literature:: Multi-step reaction with 4 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

4.1: 92 percent / TFA / CH₂Cl₂ / 0.67 h / 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; hydroxylamine hydrochloride; hydrogen bromide; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1021/jo0256078