N-(((2S,8R,9R)-14-(3-(3,5-dimethylisoxazol-4-yl)ureido)-11-isopropyl-2,9-dimethyl-12-oxo-2,3,4,5,6,8,9,10,11,12-decahydrobenzo[b][1,9,5]dioxaazacyclotetradecin-8-yl)methyl)-4-fluoro-N-methylbenzenesulfonamide

Base Information

Chemical Name:N-(((2S,8R,9R)-14-(3-(3,5-dimethylisoxazol-4-yl)ureido)-11-isopropyl-2,9-dimethyl-12-oxo-2,3,4,5,6,8,9,10,11,12-decahydrobenzo[b][1,9,5]dioxaazacyclotetradecin-8-yl)methyl)-4-fluoro-N-methylbenzenesulfonamide
CAS No.:1403478-99-8
Molecular Formula:C₃₄H₄₆FN₅O₇S
Molecular Weight:687.833
Hs Code.:

N-(((2S,8R,9R)-14-(3-(3,5-dimethylisoxazol-4-yl)ureido)-11-isopropyl-2,9-dimethyl-12-oxo-2,3,4,5,6,8,9,10,11,12-decahydrobenzo[b][1,9,5]dioxaazacyclotetradecin-8-yl)methyl)-4-fluoro-N-methylbenzenesulfonamide

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Chemical Property of N-(((2S,8R,9R)-14-(3-(3,5-dimethylisoxazol-4-yl)ureido)-11-isopropyl-2,9-dimethyl-12-oxo-2,3,4,5,6,8,9,10,11,12-decahydrobenzo[b][1,9,5]dioxaazacyclotetradecin-8-yl)methyl)-4-fluoro-N-methylbenzenesulfonamide

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Technology Process of N-(((2S,8R,9R)-14-(3-(3,5-dimethylisoxazol-4-yl)ureido)-11-isopropyl-2,9-dimethyl-12-oxo-2,3,4,5,6,8,9,10,11,12-decahydrobenzo[b][1,9,5]dioxaazacyclotetradecin-8-yl)methyl)-4-fluoro-N-methylbenzenesulfonamide

There total 12 articles about N-(((2S,8R,9R)-14-(3-(3,5-dimethylisoxazol-4-yl)ureido)-11-isopropyl-2,9-dimethyl-12-oxo-2,3,4,5,6,8,9,10,11,12-decahydrobenzo[b][1,9,5]dioxaazacyclotetradecin-8-yl)methyl)-4-fluoro-N-methylbenzenesulfonamide 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:

: 1255212-71-5
(2S,3R)-4-(tert-butoxycarbonyl(methyl)amino)-3-(tert-butyldimethylsilyloxy)-2-methylbutanoic acid

: 1403478-99-8
N-(((2S,8R,9R)-14-(3-(3,5-dimethylisoxazol-4-yl)ureido)-11-isopropyl-2,9-dimethyl-12-oxo-2,3,4,5,6,8,9,10,11,12-decahydrobenzo[b][1,9,5]dioxaazacyclotetradecin-8-yl)methyl)-4-fluoro-N-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 11 steps

1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dichloromethane / 72 h / Inert atmosphere

2: dimethylsulfide borane complex / tetrahydrofuran / 4 h / 0 - 70 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride / dichloromethane / 18 h / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h

5: sodium hydride / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

6: Hoveyda-Grubbs catalyst second generation / toluene / 18 h / Inert atmosphere

7: palladium(II) hydroxide; hydrogen / methanol / 18 h / Inert atmosphere

8: dichloromethane / 18 h / 20 °C / Inert atmosphere

9: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

10: pyridine hydrogenfluoride / tetrahydrofuran / 0.5 h

11: 2,6-dimethylpyridine / dichloromethane / 18 h / Inert atmosphere

With 2,6-dimethylpyridine; Hoveyda-Grubbs catalyst second generation; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; palladium(II) hydroxide; sodium hydride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm500994n

Reference yield:

: 1403479-92-4
tert-butyl ((2R,3S)-2-((tert-butyldimethylsilyl)oxy)-4-(isopropylamino)-3-methyl-4-oxobutyl)(methyl)carbamate

: 1403478-99-8
N-(((2S,8R,9R)-14-(3-(3,5-dimethylisoxazol-4-yl)ureido)-11-isopropyl-2,9-dimethyl-12-oxo-2,3,4,5,6,8,9,10,11,12-decahydrobenzo[b][1,9,5]dioxaazacyclotetradecin-8-yl)methyl)-4-fluoro-N-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 10 steps

1: dimethylsulfide borane complex / tetrahydrofuran / 4 h / 0 - 70 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride / dichloromethane / 18 h / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h

4: sodium hydride / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

5: Hoveyda-Grubbs catalyst second generation / toluene / 18 h / Inert atmosphere

6: palladium(II) hydroxide; hydrogen / methanol / 18 h / Inert atmosphere

7: dichloromethane / 18 h / 20 °C / Inert atmosphere

8: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

9: pyridine hydrogenfluoride / tetrahydrofuran / 0.5 h

10: 2,6-dimethylpyridine / dichloromethane / 18 h / Inert atmosphere

With 2,6-dimethylpyridine; Hoveyda-Grubbs catalyst second generation; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; palladium(II) hydroxide; sodium hydride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm500994n

Reference yield:

: 1403480-21-6
tert-butyl ((2R,3S)-2-((tert-butyldimethylsilyl)oxy)-4-(N-isopropyl-5-nitro-2-((2S)-pent-4-en-2-yloxy)benzamido)-3-methylbutyl)(methyl)carbamate

: 1403478-99-8
N-(((2S,8R,9R)-14-(3-(3,5-dimethylisoxazol-4-yl)ureido)-11-isopropyl-2,9-dimethyl-12-oxo-2,3,4,5,6,8,9,10,11,12-decahydrobenzo[b][1,9,5]dioxaazacyclotetradecin-8-yl)methyl)-4-fluoro-N-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 8 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h

2: sodium hydride / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

3: Hoveyda-Grubbs catalyst second generation / toluene / 18 h / Inert atmosphere

4: palladium(II) hydroxide; hydrogen / methanol / 18 h / Inert atmosphere

5: dichloromethane / 18 h / 20 °C / Inert atmosphere

6: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

7: pyridine hydrogenfluoride / tetrahydrofuran / 0.5 h

8: 2,6-dimethylpyridine / dichloromethane / 18 h / Inert atmosphere

With 2,6-dimethylpyridine; Hoveyda-Grubbs catalyst second generation; tetrabutyl ammonium fluoride; hydrogen; palladium(II) hydroxide; sodium hydride; pyridine hydrogenfluoride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm500994n