(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoyl-L-proline benzyl ester

Base Information

Chemical Name:(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoyl-L-proline benzyl ester
CAS No.:910316-84-6
Molecular Formula:C₂₉H₃₆N₂O₆
Molecular Weight:508.615
Hs Code.:

Synonyms:(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoyl-L-proline benzyl ester

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Chemical Property of (5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoyl-L-proline benzyl ester

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Technology Process of (5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoyl-L-proline benzyl ester

There total 3 articles about (5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoyl-L-proline benzyl ester 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: 81.0%

: 68709-76-2
5(S)-<(butyloxycarbonyl)amino>-6-phenyl-4-oxohexanoic acid

: 16652-71-4
benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

: 910316-84-6
(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoyl-L-proline benzyl ester

Guidance literature:: With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 48h;
DOI:10.1016/j.bmcl.2006.06.003

Reference yield:

: ethyl (E/Z)-(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-2-hexenoate

: 910316-84-6
(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoyl-L-proline benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / H₂ / Pd/C / ethyl acetate / 2 h / 20 °C

2: 98 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C

3: 81 percent / N-ethyl-N'-(dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate; diisopropylethylamine / dimethylformamide; CH₂Cl₂ / 48 h / 20 °C

With lithium hydroxide; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2006.06.003

Reference yield:

: 68709-74-0
ethyl (5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoate

: 910316-84-6
(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoyl-L-proline benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C

2: 81 percent / N-ethyl-N'-(dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate; diisopropylethylamine / dimethylformamide; CH₂Cl₂ / 48 h / 20 °C

With lithium hydroxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2006.06.003