Technology Process of (Z)-ethyl 6-((2R,5R,8R,11R,12S)-8-(4-hydroxybenzyl)-2-isopropyl-5,12-dimethyl-3,6,9,13-tetraoxo-1,4,7,10-tetraazacyclotridecan-11-yl)hex-4-enoate
There total 8 articles about (Z)-ethyl 6-((2R,5R,8R,11R,12S)-8-(4-hydroxybenzyl)-2-isopropyl-5,12-dimethyl-3,6,9,13-tetraoxo-1,4,7,10-tetraazacyclotridecan-11-yl)hex-4-enoate which
guide to synthetic route it.
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synthetic route:
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1449237-58-4
(Z)-ethyl 6-((2R,5R,8R,11R,12S)-8-(4-hydroxybenzyl)-2-isopropyl-5,12-dimethyl-3,6,9,13-tetraoxo-1,4,7,10-tetraazacyclotridecan-11-yl)hex-4-enoate
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
2.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
3.1: potassium hexamethylsilazane / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
4.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
5.1: hydrogenchloride / 1,4-dioxane
6.1: sodium carbonate / 1,4-dioxane; water / 2 h / 0 - 20 °C
7.1: piperidine; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; N,N-dimethyl-formamide
7.2: 16 h
8.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h
With
piperidine; hydrogenchloride; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydrogencarbonate; sodium carbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
3.1: |Wittig Olefination / 3.2: |Wittig Olefination;
DOI:10.1021/jm4008449
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1449237-58-4
(Z)-ethyl 6-((2R,5R,8R,11R,12S)-8-(4-hydroxybenzyl)-2-isopropyl-5,12-dimethyl-3,6,9,13-tetraoxo-1,4,7,10-tetraazacyclotridecan-11-yl)hex-4-enoate
- Guidance literature:
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Multi-step reaction with 7 steps
1.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
4.1: hydrogenchloride / 1,4-dioxane
5.1: sodium carbonate / 1,4-dioxane; water / 2 h / 0 - 20 °C
6.1: 2-chlorotrityl chloride polystyrene resin; N-ethyl-N,N-diisopropylamine / dichloromethane; methanol / 16 h
7.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 18 h
With
hydrogenchloride; 2-chlorotrityl chloride polystyrene resin; potassium hexamethylsilazane; sodium hydrogencarbonate; sodium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
2.1: |Wittig Olefination / 2.2: |Wittig Olefination;
DOI:10.1021/jm4008449
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1449237-58-4
(Z)-ethyl 6-((2R,5R,8R,11R,12S)-8-(4-hydroxybenzyl)-2-isopropyl-5,12-dimethyl-3,6,9,13-tetraoxo-1,4,7,10-tetraazacyclotridecan-11-yl)hex-4-enoate
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: hydrogenchloride / 1,4-dioxane
2.1: sodium carbonate / 1,4-dioxane; water / 2 h / 0 - 20 °C
3.1: piperidine; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; N,N-dimethyl-formamide
3.2: 16 h
4.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h
With
piperidine; hydrogenchloride; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm4008449
