(1S,9S)-10-Benzyl-12-ethyl-4,5-dimethoxy-1-methyl-10,12-diaza-tricyclo[7.2.2.0^2,7]trideca-2⁽⁷⁾,3,5-triene-11,13-dione

Base Information

• Chemical Name: (1S,9S)-10-Benzyl-12-ethyl-4,5-dimethoxy-1-methyl-10,12-diaza-tricyclo[7.2.2.0^2,7]trideca-2⁽⁷⁾,3,5-triene-11,13-dione
• CAS No.: 493033-47-9
• Molecular Formula: C₂₃H₂₆N₂O₄
• Molecular Weight: 394.47

Synonyms:(1S,9S)-10-Benzyl-12-ethyl-4,5-dimethoxy-1-methyl-10,12-diaza-tricyclo[7.2.2.0^2,7]trideca-2⁽⁷⁾,3,5-triene-11,13-dione

Chemical Property of (1S,9S)-10-Benzyl-12-ethyl-4,5-dimethoxy-1-methyl-10,12-diaza-tricyclo[7.2.2.0^2,7]trideca-2⁽⁷⁾,3,5-triene-11,13-dione

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Technology Process of (1S,9S)-10-Benzyl-12-ethyl-4,5-dimethoxy-1-methyl-10,12-diaza-tricyclo[7.2.2.0^2,7]trideca-2⁽⁷⁾,3,5-triene-11,13-dione

There total 5 articles about (1S,9S)-10-Benzyl-12-ethyl-4,5-dimethoxy-1-methyl-10,12-diaza-tricyclo[7.2.2.0^2,7]trideca-2⁽⁷⁾,3,5-triene-11,13-dione 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: 84.0%

pyruvoyl chloride (5704-66-5) + 2-benzylamino-3-(3,4-dimethoxy-phenyl)-N-ethyl-propionamide (493033-46-8) → (1S,9S)-10-Benzyl-12-ethyl-4,5-dimethoxy-1-methyl-10,12-diaza-tricyclo[7.2.2.02,7]trideca-2(7),3,5-triene-11,13-dione (493033-47-9)

Guidance literature:

pyruvoyl chloride; 2-benzylamino-3-(3,4-dimethoxy-phenyl)-N-ethyl-propionamide; With TEA; In dichloromethane; at 0 ℃; for 1h;

With trifluoroacetic acid; In dichloromethane; at 50 ℃; for 16h; Further stages.;

DOI:10.1021/ol0271990

Reference yield:

(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,4-dimethoxyphenyl)propanoic acid (127095-97-0) → (1S,9S)-10-Benzyl-12-ethyl-4,5-dimethoxy-1-methyl-10,12-diaza-tricyclo[7.2.2.02,7]trideca-2(7),3,5-triene-11,13-dione (493033-47-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 82 percent / TEA; HOBt; DCC / tetrahydrofuran / 16 h / 20 °C

2.1: 4 N HCl / methanol / 6 h / 20 °C

3.1: Na₂CO₃; TMOF / methanol / 16 h / 20 °C

4.1: NaBH₄ / methanol / 1 h / 20 °C

5.1: TEA / CH₂Cl₂ / 1 h / 0 °C

5.2: 84 percent / TFA / CH₂Cl₂ / 16 h / 50 °C

With hydrogenchloride; sodium tetrahydroborate; TEA; sodium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trimethyl orthoformate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol0271990

Reference yield:

2-amino-3-(3,4-dimethoxy-phenyl)-N-ethyl-propionamide → (1S,9S)-10-Benzyl-12-ethyl-4,5-dimethoxy-1-methyl-10,12-diaza-tricyclo[7.2.2.02,7]trideca-2(7),3,5-triene-11,13-dione (493033-47-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Na₂CO₃; TMOF / methanol / 16 h / 20 °C

2.1: NaBH₄ / methanol / 1 h / 20 °C

3.1: TEA / CH₂Cl₂ / 1 h / 0 °C

3.2: 84 percent / TFA / CH₂Cl₂ / 16 h / 50 °C

With sodium tetrahydroborate; TEA; sodium carbonate; trimethyl orthoformate; In methanol; dichloromethane;

DOI:10.1021/ol0271990

upstream raw materials:

pyruvoyl chloride

2-benzylamino-3-(3,4-dimethoxy-phenyl)-N-ethyl-propionamide

(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,4-dimethoxyphenyl)propanoic acid

[2-(3,4-dimethoxy-phenyl)-1-ethylcarbamoyl-ethyl]-carbamic acid tert-butyl ester

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