methyl (9R,14S)-14-[(6R)-6-(3-chlorophenyl)-2-oxo-1,3-oxazinan-3-yl]-17-cyano-5-[(methoxycarbonyl)amino]-8-(trifluoroacetyl)-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaene-9-carboxylate

Base Information

• Chemical Name: methyl (9R,14S)-14-[(6R)-6-(3-chlorophenyl)-2-oxo-1,3-oxazinan-3-yl]-17-cyano-5-[(methoxycarbonyl)amino]-8-(trifluoroacetyl)-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaene-9-carboxylate
• CAS No.: 1422510-87-9
• Molecular Formula: C₃₈H₄₄ClF₃N₆O₈Si
• Molecular Weight: 833.336

Synonyms:

Chemical Property of methyl (9R,14S)-14-[(6R)-6-(3-chlorophenyl)-2-oxo-1,3-oxazinan-3-yl]-17-cyano-5-[(methoxycarbonyl)amino]-8-(trifluoroacetyl)-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaene-9-carboxylate

Chemical Property:

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Technology Process of methyl (9R,14S)-14-[(6R)-6-(3-chlorophenyl)-2-oxo-1,3-oxazinan-3-yl]-17-cyano-5-[(methoxycarbonyl)amino]-8-(trifluoroacetyl)-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaene-9-carboxylate

There total 16 articles about methyl (9R,14S)-14-[(6R)-6-(3-chlorophenyl)-2-oxo-1,3-oxazinan-3-yl]-17-cyano-5-[(methoxycarbonyl)amino]-8-(trifluoroacetyl)-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaene-9-carboxylate 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:

1-(3-chlorophenyl)-3-iodopropan-1-one (1422510-24-4) → methyl (9R,14S)-14-[(6R)-6-(3-chlorophenyl)-2-oxo-1,3-oxazinan-3-yl]-17-cyano-5-[(methoxycarbonyl)amino]-8-(trifluoroacetyl)-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaene-9-carboxylate (1422510-87-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.25 h / 20 °C / Inert atmosphere

2.1: acetonitrile / 70 °C

3.1: tetrahydrofuran / 20 °C

3.2: 2 h / 0 - 20 °C / Inert atmosphere

With borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; acetonitrile;

Reference yield:

1-(3-chlorophenyl)-3-iodopropan-1-ol (1422509-95-2) → methyl (9R,14S)-14-[(6R)-6-(3-chlorophenyl)-2-oxo-1,3-oxazinan-3-yl]-17-cyano-5-[(methoxycarbonyl)amino]-8-(trifluoroacetyl)-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaene-9-carboxylate (1422510-87-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Jones reagent / acetone / 0.5 h / 0 °C

2.1: borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.25 h / 20 °C / Inert atmosphere

3.1: acetonitrile / 70 °C

4.1: tetrahydrofuran / 20 °C

4.2: 2 h / 0 - 20 °C / Inert atmosphere

With Jones reagent; borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; acetone; toluene; acetonitrile;

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → methyl (9R,14S)-14-[(6R)-6-(3-chlorophenyl)-2-oxo-1,3-oxazinan-3-yl]-17-cyano-5-[(methoxycarbonyl)amino]-8-(trifluoroacetyl)-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaene-9-carboxylate (1422510-87-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: N-Methyldicyclohexylamine / tetrahydrofuran / 20 h / 0 - 20 °C

2.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 18 h / 90 °C / Inert atmosphere

3.1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C

4.1: pyridine / ethyl acetate / 0 - 20 °C

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 85 °C / Inert atmosphere

6.1: hydrogen; palladium on activated charcoal / methanol / 48 h / 20 °C

7.1: N-Bromosuccinimide / chloroform / 1 h / 0 °C

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 1 h / 120 °C / Inert atmosphere; Microwave irradiation; Sealed tube

9.1: 1,1,1,3',3',3'-hexafluoro-propanol / 1.5 h / 150 °C / Microwave irradiation

10.1: acetonitrile / 70 °C

11.1: tetrahydrofuran / 20 °C

11.2: 2 h / 0 - 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; N-Bromosuccinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,1,1,3',3',3'-hexafluoro-propanol; N-Methyldicyclohexylamine; palladium on activated charcoal; hydrogen; potassium carbonate; In tetrahydrofuran; methanol; chloroform; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

1-(3-chlorophenyl)-3-iodopropan-1-one

(R)-1-(3-chlorophenyl)-3-iodopropan-1-ol

methyl (9R,14S)-14-amino-17-cyano-5-[(methoxycarbonyl)amino]-8-(trifluoroacetyl)-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaene-9-carboxylate

1-(3-chlorophenyl)-3-iodopropan-1-ol

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