N-[(1S)-1-(tert-butoxymethyl)-2-oxo-2-(2-propylanilino)ethyl]-4-[(Z)-(2,4-dioxothiazolidin-5-ylidene)methyl]benzamide

Base Information

• Chemical Name: N-[(1S)-1-(tert-butoxymethyl)-2-oxo-2-(2-propylanilino)ethyl]-4-[(Z)-(2,4-dioxothiazolidin-5-ylidene)methyl]benzamide
• CAS No.: 1352436-43-1
• Molecular Formula: C₂₇H₃₁N₃O₅S
• Molecular Weight: 509.626

Synonyms:N-[(1S)-1-(tert-butoxymethyl)-2-oxo-2-(2-propylanilino)ethyl]-4-[(Z)-(2,4-dioxothiazolidin-5-ylidene)methyl]benzamide

Chemical Property of N-[(1S)-1-(tert-butoxymethyl)-2-oxo-2-(2-propylanilino)ethyl]-4-[(Z)-(2,4-dioxothiazolidin-5-ylidene)methyl]benzamide

Chemical Property:

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Technology Process of N-[(1S)-1-(tert-butoxymethyl)-2-oxo-2-(2-propylanilino)ethyl]-4-[(Z)-(2,4-dioxothiazolidin-5-ylidene)methyl]benzamide

There total 3 articles about N-[(1S)-1-(tert-butoxymethyl)-2-oxo-2-(2-propylanilino)ethyl]-4-[(Z)-(2,4-dioxothiazolidin-5-ylidene)methyl]benzamide 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:

benzyl N-[(1S)-1-(tert-butoxymethyl)-2-oxo-2-(2-n-propylanilino)ethyl]carbamate (1352436-70-4) → N-[(1S)-1-(tert-butoxymethyl)-2-oxo-2-(2-propylanilino)ethyl]-4-[(Z)-(2,4-dioxothiazolidin-5-ylidene)methyl]benzamide (1352436-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; cyclohexene / ethyl acetate / 2 h / Inert atmosphere; Reflux

2: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU; cyclohexene; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.10.042

Reference yield:

2-propylaniline (1821-39-2) → N-[(1S)-1-(tert-butoxymethyl)-2-oxo-2-(2-propylanilino)ethyl]-4-[(Z)-(2,4-dioxothiazolidin-5-ylidene)methyl]benzamide (1352436-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; cyclohexene / ethyl acetate / 2 h / Inert atmosphere; Reflux

3: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; HATU; cyclohexene; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.10.042

Reference yield:

N-benzyloxycarbonyl-O-t-butyl-L-serine (1676-75-1) → N-[(1S)-1-(tert-butoxymethyl)-2-oxo-2-(2-propylanilino)ethyl]-4-[(Z)-(2,4-dioxothiazolidin-5-ylidene)methyl]benzamide (1352436-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; cyclohexene / ethyl acetate / 2 h / Inert atmosphere; Reflux

3: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; HATU; cyclohexene; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.10.042

upstream raw materials:

benzyl N-[(1S)-1-(tert-butoxymethyl)-2-oxo-2-(2-n-propylanilino)ethyl]carbamate

N-benzyloxycarbonyl-O-t-butyl-L-serine

2-propylaniline

Downstream raw materials:

4-[(Z)-(2,4-dioxothiazolidin-5-ylidene)methyl]-N-[(1S)-1-(hydroxymethyl)-2-oxo-2-(2-propylanilino)ethyl]benzamide

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