3,12-Bis-(3-fluoro-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-triene-7-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3,12-Bis-(3-fluoro-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-triene-7-carboxylic acid tert-butyl ester
• CAS No.: 189182-06-7
• Molecular Formula: C₃₃H₄₂F₂N₄O₂
• Molecular Weight: 564.719

Synonyms:3,12-Bis-(3-fluoro-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-triene-7-carboxylic acid tert-butyl ester

Chemical Property of 3,12-Bis-(3-fluoro-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-triene-7-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 3,12-Bis-(3-fluoro-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-triene-7-carboxylic acid tert-butyl ester

There total 8 articles about 3,12-Bis-(3-fluoro-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-triene-7-carboxylic acid tert-butyl ester 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: 94.0%

1-(Bromomethyl)-3-fluorobenzene (456-41-7) + 7-(tert-butoxycarbonyl)-3,7,12,18-tetraazabicyclo[12.3.1]octadeca-1(18),14,16-triene (182576-19-8) → 3,12-Bis-(3-fluoro-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1(18),14,16-triene-7-carboxylic acid tert-butyl ester (189182-06-7)

Guidance literature:

With potassium carbonate; In acetonitrile; Ambient temperature;

DOI:10.1021/ja964153r

Reference yield:

N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) → 3,12-Bis-(3-fluoro-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1(18),14,16-triene-7-carboxylic acid tert-butyl ester (189182-06-7)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂O / acetonitrile / Heating

2: Et₃N / tetrahydrofuran / Ambient temperature

3: 69 percent / NH₄OH / methanol / 20 h / Heating

4: 91 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

5: 73 percent / Cs₂CO₃ / dimethylformamide / 24 h / Ambient temperature

6: 72 percent / PhSH, K₂CO₃ / dimethylformamide / 2 h / Ambient temperature

7: K₂CO₃ / acetonitrile / Ambient temperature

With ammonium hydroxide; water; potassium carbonate; caesium carbonate; thiophenol; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja964153r

Reference yield:

N-[4-(trifluoroacetamido)butyl]-N-[3-(trifluoroacetamido)propyl]amine (158474-89-6) → 3,12-Bis-(3-fluoro-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1(18),14,16-triene-7-carboxylic acid tert-butyl ester (189182-06-7)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / tetrahydrofuran / Ambient temperature

2: 69 percent / NH₄OH / methanol / 20 h / Heating

3: 91 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

4: 73 percent / Cs₂CO₃ / dimethylformamide / 24 h / Ambient temperature

5: 72 percent / PhSH, K₂CO₃ / dimethylformamide / 2 h / Ambient temperature

6: K₂CO₃ / acetonitrile / Ambient temperature

With ammonium hydroxide; potassium carbonate; caesium carbonate; thiophenol; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja964153r

upstream raw materials:

1-bromomethyl-3-methyl-benzene

1-(Bromomethyl)-3-fluorobenzene

7-(tert-butoxycarbonyl)-3,7,12,18-tetraazabicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-triene

N-(3-aminopropyl)-1,4-diaminobutane

Downstream raw materials:

3,12-Bis-(3-fluoro-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-triene

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