methyl N-[(15S)-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enamido]-17,19-diazatricyclo[14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,16⁽¹⁹⁾-pentaen-5-yl]-carbamate trifluoroacetic acid salt

Base Information

• Chemical Name: methyl N-[(15S)-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enamido]-17,19-diazatricyclo[14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,16⁽¹⁹⁾-pentaen-5-yl]-carbamate trifluoroacetic acid salt
• CAS No.: 1329159-96-7
• Molecular Formula: C₂HF₃O₂*C₂₉H₃₁ClN₈O₃
• Molecular Weight: 689.094

Synonyms:

Chemical Property of methyl N-[(15S)-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enamido]-17,19-diazatricyclo[14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,16⁽¹⁹⁾-pentaen-5-yl]-carbamate trifluoroacetic acid salt

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of methyl N-[(15S)-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enamido]-17,19-diazatricyclo[14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,16⁽¹⁹⁾-pentaen-5-yl]-carbamate trifluoroacetic acid salt

There total 7 articles about methyl N-[(15S)-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enamido]-17,19-diazatricyclo[14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,16⁽¹⁹⁾-pentaen-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: 26.0%

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-[(15S)-15-amino-17,19-diazatricyclo[14.2.1.02,7]nonadeca-1(18),2,4,6,16(19)-pentaen-5-yl]carbamate bis-trifluoroacetic acid salt + trifluoroacetic acid (76-05-1) → methyl N-[(15S)-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enamido]-17,19-diazatricyclo[14.2.1.02,7]nonadeca-1(18),2,4,6,16(19)-pentaen-5-yl]-carbamate trifluoroacetic acid salt (1329159-96-7)

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-[(15S)-15-amino-17,19-diazatricyclo[14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,16⁽¹⁹⁾-pentaen-5-yl]carbamate bis-trifluoroacetic acid salt; 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-[(1S)-1-{4-[2-(hex-5-en-1-yl)-4-[(methoxycarbonyl)amino]phenyl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl}but-3-en-1-yl]carbamate → methyl N-[(15S)-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enamido]-17,19-diazatricyclo[14.2.1.02,7]nonadeca-1(18),2,4,6,16(19)-pentaen-5-yl]-carbamate trifluoroacetic acid salt (1329159-96-7)

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: palladium 10% on activated carbon; hydrogen / methanol / 2 h

3.1: hydrogenchloride / methanol; water / 4 h / 75 °C

3.2: SunFire C₁₈ column

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

4.2: SunFire C₁₈ column

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.2: |Alkene (Olefin) Metathesis;

DOI:10.1021/acs.jmedchem.6b01460

Reference yield:

C30H48N4O5Si → methyl N-[(15S)-15-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enamido]-17,19-diazatricyclo[14.2.1.02,7]nonadeca-1(18),2,4,6,16(19)-pentaen-5-yl]-carbamate trifluoroacetic acid salt (1329159-96-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride / methanol; water / 4 h / 75 °C

1.2: SunFire C₁₈ column

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 methanol; water; N,N-dimethyl-formamide;

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

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