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

Base Information

• Chemical Name: 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
• CAS No.: 389635-04-5
• Molecular Formula: C₃₄H₃₃N₃O₆
• Molecular Weight: 579.653

Synonyms: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

Chemical Property of 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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Technology Process of 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

There total 13 articles about 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 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: 91.0%

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) → 9,12-dioxo-2-oxa-10-(4'-methoxyphenyl)-11-phenyl-14-ethoxycarbonyl-18-amino-10,13-diazatricyclo[14.2.2.13,7]heneicosa-3,5,7(21),16,18,19-hexaene (389635-04-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 0.333333h;

DOI:10.1016/j.tet.2003.08.031

Reference yield:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → 9,12-dioxo-2-oxa-10-(4'-methoxyphenyl)-11-phenyl-14-ethoxycarbonyl-18-amino-10,13-diazatricyclo[14.2.2.13,7]heneicosa-3,5,7(21),16,18,19-hexaene (389635-04-5)

Guidance literature:

Multi-step reaction with 9 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

9.1: 91 percent / H₂ / Pd/C / ethanol

With sodium hydroxide; sodium tetrahydroborate; hydrogen; phosphorus tribromide; sodium hydride; potassium carbonate; triethylamine; trichlorophosphate; palladium on activated charcoal; 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) → 9,12-dioxo-2-oxa-10-(4'-methoxyphenyl)-11-phenyl-14-ethoxycarbonyl-18-amino-10,13-diazatricyclo[14.2.2.13,7]heneicosa-3,5,7(21),16,18,19-hexaene (389635-04-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NH₄Cl / toluene / 20 h / 60 °C

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

3: 91 percent / H₂ / Pd/C / ethanol / 0.33 h

With hydrogen; potassium carbonate; ammonium chloride; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; toluene; 1: Ugi reaction;

DOI:10.1016/j.tet.2003.08.031

upstream raw materials:

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

[4-(benzylideneamino)phenyl]methanol

benzaldehyde

4-methoxy-aniline

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