20-amino-4-benzyloxy-5-bromo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-11,15-dione

Base Information

• Chemical Name: 20-amino-4-benzyloxy-5-bromo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-11,15-dione
• CAS No.: 907602-56-6
• Molecular Formula: C₂₇H₂₈BrN₃O₄
• Molecular Weight: 538.441

Synonyms:20-amino-4-benzyloxy-5-bromo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-11,15-dione

Chemical Property of 20-amino-4-benzyloxy-5-bromo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-11,15-dione

Chemical Property:

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Technology Process of 20-amino-4-benzyloxy-5-bromo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-11,15-dione

There total 12 articles about 20-amino-4-benzyloxy-5-bromo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-11,15-dione 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: 55.0%

4-benzyloxy-5-bromo-20-nitro-2-oxa-10,14-diaza-tricyclo[16.2.2.13,7]tricosa-1(21),3(23),4,6,18(22),19-hexaene-11,15-dione (907602-55-5) → 20-amino-4-benzyloxy-5-bromo-2-oxa-10,14-diaza-tricyclo[16.2.2.13,7]tricosa-1(21),3(23),4,6,18(22),19-hexaene-11,15-dione (907602-56-6)

Guidance literature:

With chromium dichloride; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/jm050708u

Reference yield:

3-(4-fluoro-3-nitrophenyl)propionic acid methyl ester (907602-44-2) → 20-amino-4-benzyloxy-5-bromo-2-oxa-10,14-diaza-tricyclo[16.2.2.13,7]tricosa-1(21),3(23),4,6,18(22),19-hexaene-11,15-dione (907602-56-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / LiOH / tetrahydrofuran; methanol; H₂O

2: 93 percent / EDCI; HOBt / CH₂Cl₂ / 20 °C

3: 84 percent / 4 Angstroem sieves; CsF / dimethylsulfoxide / 20 °C

4: 55 percent / CrCl₂ / dimethylformamide / 12 h / 20 °C

With chromium dichloride; lithium hydroxide; 4 A molecular sieve; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm050708u

Reference yield:

5-(2-aminoethyl)-2-benzyloxy-3-bromophenol (907602-39-5) → 20-amino-4-benzyloxy-5-bromo-2-oxa-10,14-diaza-tricyclo[16.2.2.13,7]tricosa-1(21),3(23),4,6,18(22),19-hexaene-11,15-dione (907602-56-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: acetonitrile / 3 h

1.2: 76 percent / Na₂CO₃ / methanol; H₂O / 12 h / 20 °C

2.1: 95 percent / imidazole / dimethylformamide / 20 °C

3.1: 95 percent / CF₃CO₂H / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 92 percent / EDCI; HOBt / CH₂Cl₂ / 20 °C

5.1: 97 percent / CF₃CO₂H / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 93 percent / EDCI; HOBt / CH₂Cl₂ / 20 °C

7.1: 84 percent / 4 Angstroem sieves; CsF / dimethylsulfoxide / 20 °C

8.1: 55 percent / CrCl₂ / dimethylformamide / 12 h / 20 °C

With 1H-imidazole; chromium dichloride; 4 A molecular sieve; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; cesium fluoride; trifluoroacetic acid; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm050708u

upstream raw materials:

4-benzyloxy-5-bromo-20-nitro-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-11,15-dione

3-(4-fluoro-3-nitrophenyl)propionic acid methyl ester

5-(2-aminoethyl)-2-benzyloxy-3-bromophenol

[2-(4-benzyloxy-3-bromo-5-hydroxyphenyl)ethyl]carbamic acid tert-butyl ester

Downstream raw materials:

4-benzyloxy-5,20-dibromo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-11,15-dione

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