methyl N-[(12E,15S)-15-{[3-(3-chlorophenyl)-3-hydroxypropyl]amino}-9-oxo-17-{[2-(trimethylsilyl)ethoxy]methyl}-8,17,19-triazatricyclo[ 14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,12,16⁽¹⁹⁾-hexaen-5-yl]carbamate

Base Information

• Chemical Name: methyl N-[(12E,15S)-15-{[3-(3-chlorophenyl)-3-hydroxypropyl]amino}-9-oxo-17-{[2-(trimethylsilyl)ethoxy]methyl}-8,17,19-triazatricyclo[ 14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,12,16⁽¹⁹⁾-hexaen-5-yl]carbamate
• CAS No.: 1422510-77-7
• Molecular Formula: C₃₃H₄₄ClN₅O₅Si
• Molecular Weight: 654.281

Synonyms:methyl N-[(12E,15S)-15-{[3-(3-chlorophenyl)-3-hydroxypropyl]amino}-9-oxo-17-{[2-(trimethylsilyl)ethoxy]methyl}-8,17,19-triazatricyclo[ 14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,12,16⁽¹⁹⁾-hexaen-5-yl]carbamate

Chemical Property of methyl N-[(12E,15S)-15-{[3-(3-chlorophenyl)-3-hydroxypropyl]amino}-9-oxo-17-{[2-(trimethylsilyl)ethoxy]methyl}-8,17,19-triazatricyclo[ 14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,12,16⁽¹⁹⁾-hexaen-5-yl]carbamate

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Technology Process of methyl N-[(12E,15S)-15-{[3-(3-chlorophenyl)-3-hydroxypropyl]amino}-9-oxo-17-{[2-(trimethylsilyl)ethoxy]methyl}-8,17,19-triazatricyclo[ 14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,12,16⁽¹⁹⁾-hexaen-5-yl]carbamate

There total 11 articles about methyl N-[(12E,15S)-15-{[3-(3-chlorophenyl)-3-hydroxypropyl]amino}-9-oxo-17-{[2-(trimethylsilyl)ethoxy]methyl}-8,17,19-triazatricyclo[ 14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,12,16⁽¹⁹⁾-hexaen-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:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → methyl N-[(12E,15S)-15-{[3-(3-chlorophenyl)-3-hydroxypropyl]amino}-9-oxo-17-{[2-(trimethylsilyl)ethoxy]methyl}-8,17,19-triazatricyclo[ 14.2.1.02,7]nonadeca-1(18),2,4,6,12,16(19)-hexaen-5-yl]carbamate (1422510-77-7)

Guidance literature:

Multi-step reaction with 6 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: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / ethyl acetate / 1.08 h / -10 - 20 °C / Inert atmosphere

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid / dichloromethane / 1.5 h / 40 °C / Inert atmosphere

5.1: 1,1,1,3',3',3'-hexafluoro-propanol / 1 h / 150 °C / Microwave irradiation

6.1: potassium carbonate / acetonitrile / 75 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 1,1,1,3',3',3'-hexafluoro-propanol; sodium hydride; potassium carbonate; ammonium chloride; toluene-4-sulfonic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile;

Reference yield:

methyl N-(4-(2-((1S)-1-((tert-butoxycarbonyl)amino)but-3-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)-3-nitrophenyl)carbamate (1422387-43-6) → methyl N-[(12E,15S)-15-{[3-(3-chlorophenyl)-3-hydroxypropyl]amino}-9-oxo-17-{[2-(trimethylsilyl)ethoxy]methyl}-8,17,19-triazatricyclo[ 14.2.1.02,7]nonadeca-1(18),2,4,6,12,16(19)-hexaen-5-yl]carbamate (1422510-77-7)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / ethyl acetate / 1.08 h / -10 - 20 °C / Inert atmosphere

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid / dichloromethane / 1.5 h / 40 °C / Inert atmosphere

4: 1,1,1,3',3',3'-hexafluoro-propanol / 1 h / 150 °C / Microwave irradiation

5: potassium carbonate / acetonitrile / 75 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 1,1,1,3',3',3'-hexafluoro-propanol; potassium carbonate; ammonium chloride; toluene-4-sulfonic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; zinc; In methanol; dichloromethane; ethyl acetate; acetonitrile;

Reference yield:

methyl N-(4-(2-((1S)-1-((tert-butoxycarbonyl)amino)but-3-en-1-yl)-1H-imidazol-5-yl)-3-nitrophenyl)carbamate (1422387-42-5) → methyl N-[(12E,15S)-15-{[3-(3-chlorophenyl)-3-hydroxypropyl]amino}-9-oxo-17-{[2-(trimethylsilyl)ethoxy]methyl}-8,17,19-triazatricyclo[ 14.2.1.02,7]nonadeca-1(18),2,4,6,12,16(19)-hexaen-5-yl]carbamate (1422510-77-7)

Guidance literature:

Multi-step reaction with 6 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: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / ethyl acetate / 1.08 h / -10 - 20 °C / Inert atmosphere

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid / dichloromethane / 1.5 h / 40 °C / Inert atmosphere

5.1: 1,1,1,3',3',3'-hexafluoro-propanol / 1 h / 150 °C / Microwave irradiation

6.1: potassium carbonate / acetonitrile / 75 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 1,1,1,3',3',3'-hexafluoro-propanol; sodium hydride; potassium carbonate; ammonium chloride; toluene-4-sulfonic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile;

upstream raw materials:

methyl N-(4-(2-((1S)-1-((tert-butoxycarbonyl)amino)but-3-en-1-yl)-1H-imidazol-5-yl)-3-nitrophenyl)carbamate

methyl N-(4-(2-((1S)-1-((tert-butoxycarbonyl)amino)but-3-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)-3-nitrophenyl)carbamate

(2-trimethylethylsilylethoxy)methyl chloride

tert-butyl N-[(1S)-1-(4-{2-amino-4-[(methoxycarbonyl)-amino]phenyl}-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)but-3-en-1-yl]carbamate

Downstream raw materials:

methyl N-[(12E,15S)-15-[6-(3-chlorophenyl)-2-oxo-1,3-oxazinan-3-yl]-9-oxo-8,17,19-triazatricyclo[ 14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,12,16⁽¹⁹⁾-hexaen-5-yl]carbamate hydrochloride

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