Technology Process of (3S)-1-[(2S,3S)-2-amino-3-[4-(5-bromo-6-oxo-1,6-dihydroypyridin-3-yl)phenyl]-1-oxobutanyl]-3-fluoropyrrolidine trifluoroacetic acid salt
There total 8 articles about (3S)-1-[(2S,3S)-2-amino-3-[4-(5-bromo-6-oxo-1,6-dihydroypyridin-3-yl)phenyl]-1-oxobutanyl]-3-fluoropyrrolidine trifluoroacetic acid salt which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(3S)-1-[(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(6-oxo-1,6-dihydroypyridin-3-yl)phenyl]-1-oxobutanyl]-3-fluoropyrrolidine;
With
pyridinium hydrobromide perbromide;
In
dichloromethane;
at 20 ℃;
for 2h;
trifluoroacetic acid;
In
dichloromethane;
at 20 ℃;
for 1h;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: tetramethylguanidinum azide / acetonitrile / 12 h / 20 °C
2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 4.25 h / 0 °C
3.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine / DMF (N,N-dimethyl-formamide) / 12 h / 20 °C
3.2: 12 h / 90 °C
3.3: 12 h / 20 °C
4.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / ethanol; water; toluene / 12 h / 90 °C
5.1: pyridine hydrochloride / 0.33 h / 160 °C / Neat (no solvent)
5.2: 12 h / 20 °C
6.1: pyridinium hydrobromide perbromide / dichloromethane / 2 h / 20 °C
6.2: 1 h / 20 °C
With
lithium hydroxide; pyridinium hydrobromide perbromide; dihydrogen peroxide; pyridine hydrochloride; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; tetramethylguanidinum azide;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; DMF (N,N-dimethyl-formamide); ethanol; dichloromethane; water; toluene; acetonitrile;
4.1: Suzuki Coupling;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: copper (II) bromide dimethylsulfide / tetrahydrofuran; dimethylsulfide; diethyl ether / 0.5 h / -40 °C
1.2: 15 h / -20 - 20 °C
2.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 - 0 °C
2.2: 4 h / -78 - 0 °C
3.1: tetramethylguanidinum azide / acetonitrile / 12 h / 20 °C
4.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 4.25 h / 0 °C
5.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine / DMF (N,N-dimethyl-formamide) / 12 h / 20 °C
5.2: 12 h / 90 °C
5.3: 12 h / 20 °C
6.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / ethanol; water; toluene / 12 h / 90 °C
7.1: pyridine hydrochloride / 0.33 h / 160 °C / Neat (no solvent)
7.2: 12 h / 20 °C
8.1: pyridinium hydrobromide perbromide / dichloromethane / 2 h / 20 °C
8.2: 1 h / 20 °C
With
lithium hydroxide; pyridinium hydrobromide perbromide; copper (II) bromide dimethylsulfide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; pyridine hydrochloride; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; tetramethylguanidinum azide;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; DMF (N,N-dimethyl-formamide); dimethylsulfide; diethyl ether; ethanol; dichloromethane; water; toluene; acetonitrile;
6.1: Suzuki Coupling;