methyl N-[(12E,15S)-15-[4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-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-[4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-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.: 1422510-90-4
• Molecular Formula: C₃₅H₄₄ClN₅O₅Si
• Molecular Weight: 678.303

Synonyms:methyl N-[(12E,15S)-15-[4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-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-[4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-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-[4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-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 15 articles about methyl N-[(12E,15S)-15-[4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-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: 100.0%

methyl 3-(3-chlorophenyl)-5-{[(12E,15S)-5-[(methoxycarbonyl)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-15-yl]amino}pentanoate bistrifluoroacetate → methyl N-[(12E,15S)-15-[4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-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 (1422510-90-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In toluene; at 150 ℃; for 16h; Sealed tube;

Reference yield: 18.0%

methyl N-[(12E,15S)-15-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 (1422510-76-6) + methyl 3-(3-chlorophenyl)-5-((methylsulfonyl)oxy)pentanoate (1422510-00-6) → methyl 3-(3-chlorophenyl)-5-{[(12E,15S)-5-[(methoxycarbonyl)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-15-yl]amino}pentanoate bistrifluoroacetate + methyl N-[(12E,15S)-15-[4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-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 (1422510-90-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In toluene; at 120 ℃; for 18h; Sealed tube;

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → methyl N-[(12E,15S)-15-[4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-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 (1422510-90-4)

Guidance literature:

Multi-step reaction with 7 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: N-ethyl-N,N-diisopropylamine / toluene / 18 h / 120 °C / Sealed tube

7.1: N-ethyl-N,N-diisopropylamine / toluene / 16 h / 150 °C / Sealed tube

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; 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; toluene;

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

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