methyl N-[(10R,14S)-14-[6-(2-fluoro-3-methoxyphenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaen-5-yl]carbamate

Base Information

• Chemical Name: methyl N-[(10R,14S)-14-[6-(2-fluoro-3-methoxyphenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaen-5-yl]carbamate
• CAS No.: 1422511-03-2
• Molecular Formula: C₃₅H₄₆FN₅O₇Si
• Molecular Weight: 695.863

Synonyms:methyl N-[(10R,14S)-14-[6-(2-fluoro-3-methoxyphenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaen-5-yl]carbamate

Chemical Property of methyl N-[(10R,14S)-14-[6-(2-fluoro-3-methoxyphenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaen-5-yl]carbamate

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Technology Process of methyl N-[(10R,14S)-14-[6-(2-fluoro-3-methoxyphenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaen-5-yl]carbamate

There total 19 articles about methyl N-[(10R,14S)-14-[6-(2-fluoro-3-methoxyphenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaen-5-yl]carbamate 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: 71.0%

methyl N-[(10R,14S)-14-{[3-(2-fluoro-3-methoxyphenyl)-3-hydroxypropyl]amino}-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaen-5-yl]carbamate + 1,1'-carbonyldiimidazole (530-62-1) → methyl N-[(10R,14S)-14-[6-(2-fluoro-3-methoxyphenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaen-5-yl]carbamate (1422511-03-2)

Guidance literature:

methyl N-[(10R,14S)-14-{[3-(2-fluoro-3-methoxyphenyl)-3-hydroxypropyl]amino}-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaen-5-yl]carbamate; 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.25h; Inert atmosphere;

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → methyl N-[(10R,14S)-14-[6-(2-fluoro-3-methoxyphenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaen-5-yl]carbamate (1422511-03-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C

1.2: 1 h / 0 °C

2.1: zinc; ammonium chloride / methanol / 4 h / 60 °C / Sealed tube

3.1: triethylamine / ethyl acetate / 0.5 h / 0 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / dichloromethane / 0.67 h / 40 °C / Inert atmosphere

4.2: 40 °C / Inert atmosphere

5.1: hydrogen; palladium on activated charcoal / methanol / 20 °C / Inert atmosphere

6.1: lithium hydroxide; water / methanol / 1 h / 60 °C

7.1: dmap; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 96 h / 20 - 50 °C

8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

9.1: potassium carbonate / acetonitrile / 75 °C

10.1: tetrahydrofuran / 20 °C / Inert atmosphere

10.2: 0.25 h / 0 °C / Inert atmosphere

With dmap; palladium on activated charcoal; water; hydrogen; sodium hydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ammonium chloride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; zinc; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

tert-butyl 3-(2-fluoro-3-methoxyphenyl)-3-hydroxypropanoate (1422510-38-0) → methyl N-[(10R,14S)-14-[6-(2-fluoro-3-methoxyphenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaen-5-yl]carbamate (1422511-03-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

2.1: 1H-imidazole; triphenylphosphine; iodine / benzene / 20 °C

3.1: potassium carbonate / acetonitrile / 75 °C

4.1: tetrahydrofuran / 20 °C / Inert atmosphere

4.2: 0.25 h / 0 °C / Inert atmosphere

With 1H-imidazole; lithium aluminium tetrahydride; iodine; potassium carbonate; triphenylphosphine; In tetrahydrofuran; acetonitrile; benzene;

upstream raw materials:

2-fluoro-3-methoxybenzaldehyde

tert-butyl 3-(2-fluoro-3-methoxyphenyl)-3-hydroxypropanoate

1-(2-fluoro-3-methoxyphenyl)propan-1,3-diol

1-(2-fluoro-3-methoxyphenyl)-3-iodopropan-1-ol

Downstream raw materials:

methyl N-[(10R,14S)-14-[6-(2-fluoro-3-methoxyphenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaen-5-yl]carbamate trifluoroacetate

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