(8S,11R)-11-Benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methyl ester

Base Information

• Chemical Name: (8S,11R)-11-Benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methyl ester
• CAS No.: 168292-12-4
• Molecular Formula: C₂₇H₂₅N₃O₈
• Molecular Weight: 519.511

Synonyms:(8S,11R)-11-Benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methyl ester

Chemical Property of (8S,11R)-11-Benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methyl ester

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Technology Process of (8S,11R)-11-Benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methyl ester

There total 6 articles about (8S,11R)-11-Benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methyl 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: 81.0%

(S)-{(R)-2-[2-(5-Fluoro-2-nitro-phenyl)-acetylamino]-3-phenyl-propionylamino}-(3-hydroxy-5-methoxy-phenyl)-acetic acid methyl ester (168292-22-6) → (8S,11R)-11-Benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-8-carboxylic acid methyl ester (168292-12-4)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In tetrahydrofuran; for 20h; Ambient temperature;

DOI:10.1021/jo00125a026

Reference yield:

(5-Fluoro-2-nitro-phenyl)-acetic Acid (29640-98-0) → (8S,11R)-11-Benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-8-carboxylic acid methyl ester (168292-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N, EDC / CH₂Cl₂ / 2 h / Ambient temperature

2: 91 percent / BBr₃ / CH₂Cl₂ / 0.12 h / -78 °C

3: 81 percent / K₂CO₃, 18-crown-6 / tetrahydrofuran / 20 h / Ambient temperature

With 18-crown-6 ether; boron tribromide; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00125a026

Reference yield:

methyl 2-(5-fluoro-2-nitrophenyl)acetate (29640-99-1) → (8S,11R)-11-Benzyl-5-methoxy-16-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-8-carboxylic acid methyl ester (168292-12-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / 6 N HCl / Heating

2: Et₃N, EDC / CH₂Cl₂ / 2 h / Ambient temperature

3: 91 percent / BBr₃ / CH₂Cl₂ / 0.12 h / -78 °C

4: 81 percent / K₂CO₃, 18-crown-6 / tetrahydrofuran / 20 h / Ambient temperature

With hydrogenchloride; 18-crown-6 ether; boron tribromide; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00125a026

upstream raw materials:

(S)-{(R)-2-[2-(5-Fluoro-2-nitro-phenyl)-acetylamino]-3-phenyl-propionylamino}-(3-hydroxy-5-methoxy-phenyl)-acetic acid methyl ester

(5-Fluoro-2-nitro-phenyl)-acetic Acid

methyl 2-(5-fluoro-2-nitrophenyl)acetate

methyl (3-fluorophenyl)acetate

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