4-benzyloxy-5-bromo-16-nitro-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one

Base Information

• Chemical Name: 4-benzyloxy-5-bromo-16-nitro-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one
• CAS No.: 907602-45-3
• Molecular Formula: C₂₄H₂₁BrN₂O₅
• Molecular Weight: 497.345

Synonyms:4-benzyloxy-5-bromo-16-nitro-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one

Chemical Property of 4-benzyloxy-5-bromo-16-nitro-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one

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Technology Process of 4-benzyloxy-5-bromo-16-nitro-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one

There total 6 articles about 4-benzyloxy-5-bromo-16-nitro-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one 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: 85.0%

N-[2-(4-benzyloxy-3-bromo-5-hydroxy-phenyl)-ethyl]-3-(4-fluoro-3-nitro-phenyl)-propionamide (907602-40-8) → 4-benzyloxy-5-bromo-16-nitro-2-oxa-10-aza-tricyclo[12.2.2.13,7]-nonadeca-1(17),3(19),4,6,14(18),15-hexaen-11-one (907602-45-3)

Guidance literature:

With 4 A molecular sieve; potassium carbonate; In dimethyl sulfoxide; at 20 ℃; for 3h;

DOI:10.1021/jm050708u

Reference yield:

3-(4-fluoro-3-nitrophenyl)propionic acid methyl ester (907602-44-2) → 4-benzyloxy-5-bromo-16-nitro-2-oxa-10-aza-tricyclo[12.2.2.13,7]-nonadeca-1(17),3(19),4,6,14(18),15-hexaen-11-one (907602-45-3)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 72 percent / HOBt; EDCI / CH₂Cl₂ / 1 h / 20 °C

3: 85 percent / K₂CO₃; 4 Angstroem sieves / dimethylsulfoxide / 3 h / 20 °C

With lithium hydroxide; 4 A molecular sieve; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/jm050708u

Reference yield:

5-(2-aminoethyl)-2-benzyloxy-3-bromophenol (907602-39-5) → 4-benzyloxy-5-bromo-16-nitro-2-oxa-10-aza-tricyclo[12.2.2.13,7]-nonadeca-1(17),3(19),4,6,14(18),15-hexaen-11-one (907602-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / HOBt; EDCI / CH₂Cl₂ / 1 h / 20 °C

2: 85 percent / K₂CO₃; 4 Angstroem sieves / dimethylsulfoxide / 3 h / 20 °C

With 4 A molecular sieve; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jm050708u

upstream raw materials:

N-[2-(4-benzyloxy-3-bromo-5-hydroxy-phenyl)-ethyl]-3-(4-fluoro-3-nitro-phenyl)-propionamide

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

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

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

Downstream raw materials:

5,16-dibromo-4-benzyloxy-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one

4-benzyloxy-5-bromo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one

16-amino-4-benzyloxy-5-bromo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]-nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaen-11-one

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