N-{4-[[(R)-2-Hydroxy-2-((10S,13S)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl)-ethyl]-(3-methyl-butyl)-sulfamoyl]-phenyl}-acetamide

Base Information

• Chemical Name: N-{4-[[(R)-2-Hydroxy-2-((10S,13S)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl)-ethyl]-(3-methyl-butyl)-sulfamoyl]-phenyl}-acetamide
• CAS No.: 679402-80-3
• Molecular Formula: C₃₄H₅₀N₄O₇S
• Molecular Weight: 658.86

Synonyms:N-{4-[[(R)-2-Hydroxy-2-((10S,13S)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl)-ethyl]-(3-methyl-butyl)-sulfamoyl]-phenyl}-acetamide

Chemical Property of N-{4-[[(R)-2-Hydroxy-2-((10S,13S)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl)-ethyl]-(3-methyl-butyl)-sulfamoyl]-phenyl}-acetamide

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Technology Process of N-{4-[[(R)-2-Hydroxy-2-((10S,13S)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl)-ethyl]-(3-methyl-butyl)-sulfamoyl]-phenyl}-acetamide

There total 7 articles about N-{4-[[(R)-2-Hydroxy-2-((10S,13S)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl)-ethyl]-(3-methyl-butyl)-sulfamoyl]-phenyl}-acetamide 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:

p-acetylaminobenzenesulfonyl chloride (121-60-8) + (10S,13S,1'R)-13-[1'-hydroxy-2'-(1''-amino-3''-methylbutyl)ethyl]-8,11-dioxo-10-isopropyl-2-oxa-9,12-diazabicyclo[13.2.2]nonadeca-15,17,18-triene (301210-56-0) → N-{4-[[(R)-2-Hydroxy-2-((10S,13S)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-13-yl)-ethyl]-(3-methyl-butyl)-sulfamoyl]-phenyl}-acetamide (679402-80-3)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jm030337m

Reference yield:

1-amino-3-methylbutane (107-85-7) → N-{4-[[(R)-2-Hydroxy-2-((10S,13S)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-13-yl)-ethyl]-(3-methyl-butyl)-sulfamoyl]-phenyl}-acetamide (679402-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / dimethylsulfoxide / 30 h / 80 °C

2: aq. NaHCO₃ / tetrahydrofuran / 20 °C

With sodium hydrogencarbonate; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1021/jm030337m

Reference yield:

10S-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-13S-carboxylic acid (180078-24-4) → N-{4-[[(R)-2-Hydroxy-2-((10S,13S)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-13-yl)-ethyl]-(3-methyl-butyl)-sulfamoyl]-phenyl}-acetamide (679402-80-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N-methylpiperidine / tetrahydrofuran / -15 °C

1.2: isobutyl chloroformate / tetrahydrofuran / 0.08 h / -15 °C

1.3: 90 percent / tetrahydrofuran; diethyl ether / -15 - 20 °C

2.1: HBr / tetrahydrofuran; ethyl acetate / 0.03 h / 10 °C

3.1: 360 mg / NaBH₄ / ethanol / 0.17 h / -10 °C

4.1: 98 percent / NaOMe / methanol; tetrahydrofuran / 0.25 h / 20 °C

5.1: 92 percent / dimethylsulfoxide / 30 h / 80 °C

6.1: aq. NaHCO₃ / tetrahydrofuran / 20 °C

With N-methylcyclohexylamine; sodium tetrahydroborate; hydrogen bromide; sodium methylate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/jm030337m

upstream raw materials:

p-acetylaminobenzenesulfonyl chloride

(10S,13S,1'R)-13-[1'-hydroxy-2'-(1''-amino-3''-methylbutyl)ethyl]-8,11-dioxo-10-isopropyl-2-oxa-9,12-diazabicyclo[13.2.2]nonadeca-15,17,18-triene

1-amino-3-methylbutane

10S-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-13S-carboxylic acid

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