10-(4-methoxy-phenyl)-19-nitro-9,12-dioxo-11-phenyl-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]heneicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid ethyl ester

Base Information

• Chemical Name: 10-(4-methoxy-phenyl)-19-nitro-9,12-dioxo-11-phenyl-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]heneicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid ethyl ester
• CAS No.: 390360-63-1
• Molecular Formula: C₃₄H₃₁N₃O₈
• Molecular Weight: 609.635

Synonyms:

Chemical Property of 10-(4-methoxy-phenyl)-19-nitro-9,12-dioxo-11-phenyl-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]heneicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid ethyl ester

Chemical Property:

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Technology Process of 10-(4-methoxy-phenyl)-19-nitro-9,12-dioxo-11-phenyl-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]heneicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid ethyl ester

There total 12 articles about 10-(4-methoxy-phenyl)-19-nitro-9,12-dioxo-11-phenyl-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]heneicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid ethyl 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: 65.0%

3-(4-Fluoro-3-nitro-phenyl)-2-{2-[[2-(3-hydroxy-phenyl)-acetyl]-(4-methoxy-phenyl)-amino]-2-phenyl-acetylamino}-propionic acid ethyl ester (627535-85-7) → 10-(4-methoxy-phenyl)-19-nitro-9,12-dioxo-11-phenyl-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]heneicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid ethyl ester (390360-63-1,390360-65-3,390360-67-5,390360-69-7,628308-40-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2003.08.031

Reference yield:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → 10-(4-methoxy-phenyl)-19-nitro-9,12-dioxo-11-phenyl-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]heneicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid ethyl ester (390360-63-1,390360-65-3,390360-67-5,390360-69-7,628308-40-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 82 percent / NaBH₄ / methanol / 1 h / 0 °C

2.1: 75 percent / PBr₃ / toluene / 5 h / 20 °C

3.1: 92 percent / NaH / dimethylformamide / 1 h / 20 °C

4.1: aq. NaOH / ethanol / 1 h / 20 °C

5.1: 35 mg / dioxane / 3 h / Heating

6.1: 91 percent / POCl₃; Et₃N / CH₂Cl₂ / 5 h / -25 °C

7.1: toluene / 20 °C

7.2: 65 percent / NH₄Cl / toluene / 20 h / 60 °C

8.1: 65 percent / potassium carbonate / dimethylformamide / 20 °C

With sodium hydroxide; sodium tetrahydroborate; phosphorus tribromide; sodium hydride; potassium carbonate; triethylamine; trichlorophosphate; In 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 7.2: Ugi reaction;

DOI:10.1021/ol0168420

Reference yield:

3-(4-fluoro-3-nitrophenyl)-2-isocyanopropionic acid ethyl ester (389634-82-6) → 10-(4-methoxy-phenyl)-19-nitro-9,12-dioxo-11-phenyl-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]heneicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid ethyl ester (390360-63-1,390360-65-3,390360-67-5,390360-69-7,628308-40-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₄Cl / toluene / 20 h / 60 °C

2: 65 percent / K₂CO₃ / dimethylformamide / 3 h / 20 °C

With potassium carbonate; ammonium chloride; In N,N-dimethyl-formamide; toluene; 1: Ugi reaction;

DOI:10.1016/j.tet.2003.08.031

upstream raw materials:

3-(4-Fluoro-3-nitro-phenyl)-2-{2-[[2-(3-hydroxy-phenyl)-acetyl]-(4-methoxy-phenyl)-amino]-2-phenyl-acetylamino}-propionic acid ethyl ester

[4-(benzylideneamino)phenyl]methanol

benzaldehyde

4-methoxy-aniline

Downstream raw materials:

9,12-dioxo-2-oxa-10-(4'-methoxyphenyl)-11-phenyl-14-ethoxycarbonyl-18-amino-10,13-diazatricyclo[14.2.2.1^3,7]heneicosa-3,5,7⁽²¹⁾,16,18,19-hexaene

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