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-[14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,12,16⁽¹⁹⁾-hexaen-5-yl]-carbamate trifluoroacetic acid salt

Base Information

• Chemical Name: methyl N-[(12E,15S)-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.: 1329160-22-6
• Molecular Formula: C₂HF₃O₂*C₂₈H₂₆ClN₉O₄
• Molecular Weight: 702.049

Synonyms: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-[14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,12,16⁽¹⁹⁾-hexaen-5-yl]-carbamate trifluoroacetic acid salt

Chemical Property of methyl N-[(12E,15S)-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:

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Technology Process of 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-[14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,12,16⁽¹⁹⁾-hexaen-5-yl]-carbamate trifluoroacetic acid salt

There total 6 articles about 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-[14.2.1.0^2,7]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: 28.0%

2,5-dioxopyrrolidin-1-yl (2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enoate (1094107-15-9) + methyl N-[(12E,15S)-15-amino-9-oxo-8,17,19-triazatricyclo[14.2.1.02,7]nonadeca-1(18),2,4,6,12,16(19)-hexaen-5-yl]-carbamate dihydrochloride + trifluoroacetic acid (76-05-1) → 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)

Guidance literature:

2,5-dioxopyrrolidin-1-yl (2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enoate; methyl N-[(12E,15S)-15-amino-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 dihydrochloride; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1.5h;

trifluoroacetic acid; In water; acetonitrile;

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)-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)

Guidance literature:

Multi-step reaction with 2 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

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.6b01460

Reference yield:

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 (1329167-29-4) → 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)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper(l) iodide; L-proline; ammonium hydroxide; potassium carbonate / dimethyl sulfoxide / 20 h / 85 °C / Inert atmosphere; Sealed tube

2.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / ethyl acetate / 2 h / -10 - 20 °C

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

3.2: 1.5 h / Reflux

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

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

5.2: SunFire C₁₈ column

With hydrogenchloride; ammonium hydroxide; copper(l) iodide; potassium carbonate; toluene-4-sulfonic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; L-proline; In 1,4-dioxane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; 3.2: |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

trifluoroacetic acid

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

Downstream raw materials:

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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