methyl N-[(12E,15S)-18-chloro-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)-phenyl]prop-2-enamido]-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 trifluoroacetic acid salt

Base Information

• Chemical Name: methyl N-[(12E,15S)-18-chloro-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)-phenyl]prop-2-enamido]-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 trifluoroacetic acid salt
• CAS No.: 1329160-94-2
• Molecular Formula: C₂HF₃O₂*C₂₈H₂₅Cl₂N₉O₄
• Molecular Weight: 736.494

Synonyms:methyl N-[(12E,15S)-18-chloro-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)-phenyl]prop-2-enamido]-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 trifluoroacetic acid salt

Chemical Property of methyl N-[(12E,15S)-18-chloro-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)-phenyl]prop-2-enamido]-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 trifluoroacetic acid salt

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Technology Process of methyl N-[(12E,15S)-18-chloro-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)-phenyl]prop-2-enamido]-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 trifluoroacetic acid salt

There total 7 articles about methyl N-[(12E,15S)-18-chloro-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)-phenyl]prop-2-enamido]-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 trifluoroacetic acid salt 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: 44.0%

methyl N-[(12E,15S)-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enamido]-9-oxo-8,17,19-triazatricyclo-[14.2.1.02,7]nonadeca-1(18),2,4,6,12,16(19)-hexaen-5-yl]-carbamate trifluoroacetic acid salt (1329160-22-6) → methyl N-[(12E,15S)-18-chloro-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)-phenyl]prop-2-enamido]-9-oxo-8,17,19-triazatricyclo[14.2.1.02,7]nonadeca-1(18),2,4,6,12,16(19)-hexaen-5-yl]carbamate trifluoroacetic acid salt (1329160-94-2)

Guidance literature:

With N-chloro-succinimide; In chloroform; acetonitrile; at 65 ℃; for 5h; Sealed tube;

DOI:10.1021/acs.jmedchem.6b01460

Reference yield:

tert-butyl N-[(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]-carbamate (1422387-49-2) → methyl N-[(12E,15S)-18-chloro-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)-phenyl]prop-2-enamido]-9-oxo-8,17,19-triazatricyclo[14.2.1.02,7]nonadeca-1(18),2,4,6,12,16(19)-hexaen-5-yl]carbamate trifluoroacetic acid salt (1329160-94-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / 1,4-dioxane / 2 h / 75 °C / Sealed tube

2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C

2.2: SunFire C₁₈ column

3.1: N-chloro-succinimide / acetonitrile; chloroform / 5 h / 65 °C / Sealed tube

With hydrogenchloride; N-chloro-succinimide; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; chloroform; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.6b01460

Reference yield:

tert-butyl N-[(1S)-1-(4-{4-[(methoxycarbonyl)amino]-2-(pent-4-enamido)phenyl}-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)but-3-en-1-yl]carbamate (1422387-48-1) → methyl N-[(12E,15S)-18-chloro-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)-phenyl]prop-2-enamido]-9-oxo-8,17,19-triazatricyclo[14.2.1.02,7]nonadeca-1(18),2,4,6,12,16(19)-hexaen-5-yl]carbamate trifluoroacetic acid salt (1329160-94-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 40 °C

1.2: 1.5 h / Reflux

2.1: hydrogenchloride / 1,4-dioxane / 2 h / 75 °C / Sealed tube

3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C

3.2: SunFire C₁₈ column

4.1: N-chloro-succinimide / acetonitrile; chloroform / 5 h / 65 °C / Sealed tube

With hydrogenchloride; N-chloro-succinimide; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile; 1.2: |Alkene (Olefin) Metathesis;

DOI:10.1021/acs.jmedchem.6b01460

upstream raw materials:

2,5-dioxopyrrolidin-1-yl (2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enoate

tert-butyl N-[(12E,15S)-5-[(methoxycarbonyl)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-15-yl]-carbamate

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

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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