N-[(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-2,13-dioxo-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-trien-16-yl]-N-methyl-methanesulfonamide

Base Information

• Chemical Name: N-[(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-2,13-dioxo-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-trien-16-yl]-N-methyl-methanesulfonamide
• CAS No.: 1385067-91-3
• Molecular Formula: C₂₆H₃₆N₄O₆S
• Molecular Weight: 532.661

Synonyms:N-[(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-2,13-dioxo-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-trien-16-yl]-N-methyl-methanesulfonamide

Chemical Property of N-[(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-2,13-dioxo-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-trien-16-yl]-N-methyl-methanesulfonamide

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Technology Process of N-[(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-2,13-dioxo-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-trien-16-yl]-N-methyl-methanesulfonamide

There total 7 articles about N-[(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-2,13-dioxo-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-trien-16-yl]-N-methyl-methanesulfonamide 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: 51.0%

C26H35N3O9S2 + benzylamine (100-46-9) → N-[(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-2,13-dioxo-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1(18),14,16-trien-16-yl]-N-methyl-methanesulfonamide (1385067-91-3)

Guidance literature:

In ethanol; for 24h; Reflux;

DOI:10.1016/j.bmc.2012.05.039

Reference yield:

(S)-2-(allyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanamine (1385068-39-2) → N-[(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-2,13-dioxo-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1(18),14,16-trien-16-yl]-N-methyl-methanesulfonamide (1385067-91-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium hydroxide / 1,4-dioxane; water / 1.17 h / 20 °C

1.2: 16 h / 20 °C

2.1: acetic acid / water / 1.75 h / 60 °C

3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / Inert atmosphere; Reflux

4.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / 760.05 Torr

5.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 23 h / 20 °C

6.1: ethanol / 24 h / Reflux

With Hoveyda-Grubbs catalyst second generation; palladium 10% on activated carbon; hydrogen; di(n-butyl)tin oxide; acetic acid; triethylamine; lithium hydroxide; In 1,4-dioxane; methanol; ethanol; dichloromethane; water;

DOI:10.1016/j.bmc.2012.05.039

Reference yield:

methyl 3-(but-3-en-1-ylcarbamoyl)-5-(n-methylmethyl-sulfonamido)benzoate (1385068-88-1) → N-[(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-2,13-dioxo-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1(18),14,16-trien-16-yl]-N-methyl-methanesulfonamide (1385067-91-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium hydroxide / 1,4-dioxane; water / 1.17 h / 20 °C

1.2: 16 h / 20 °C

2.1: acetic acid / water / 1.75 h / 60 °C

3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / Inert atmosphere; Reflux

4.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / 760.05 Torr

5.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 23 h / 20 °C

6.1: ethanol / 24 h / Reflux

With Hoveyda-Grubbs catalyst second generation; palladium 10% on activated carbon; hydrogen; di(n-butyl)tin oxide; acetic acid; triethylamine; lithium hydroxide; In 1,4-dioxane; methanol; ethanol; dichloromethane; water;

DOI:10.1016/j.bmc.2012.05.039

upstream raw materials:

benzylamine

(S)-2-(allyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanamine

methyl 3-(but-3-en-1-ylcarbamoyl)-5-(n-methylmethyl-sulfonamido)benzoate

N₁-((S)-2-allyloxy-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-ethyl)-N₃-but-3-enyl-5-(methanesulfonyl-methyl-amino)-isophthalamide

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