Hydrochloric Acid → (1R,2S)-3-fluoro-1-hydroxy-1-(4-(3-(methylsulfonamidomethyl)isoxazol-5-yl)phenyl)propan-2-aminium chloride
Reaktionsgleichung
[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:18][N:17]=[C:16]([CH2:19][NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=3)=[CH:10][CH:9]=2)[O:6]C(C)(C)[N:4]1C(OC(C)(C)C)=O.[ClH:34].O>O1CCOCC1>[Cl-:34].[F:1][CH2:2][C@@H:3]([NH3+:4])[C@H:7]([OH:6])[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([CH2:19][NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=2)=[CH:10][CH:9]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To (4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-(methylsulfonamido-methyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylate (300 mg, 0.62 mmol) is added 4N HCl in dioxane (4 ml) at room temperature. The solution is then cooled to 0° C. and water (0.5 ml) is added. The ice bath is removed after ten minutes and the reaction is stirred at room temperature for one hour. The volatiles were then removed by rotary evaporation. Several evaporation cycles were performed using acetonitrile to ensure complete removal of water and excess HCl gave the title compound (234 mg): m/z (Cl) 344 ([M+H]+.
Aufarbeitung
- customThe ice bath is removed after ten minutes
- customThe volatiles were then removed by rotary evaporation
- customSeveral evaporation cycles
- customremoval of water and excess HCl
Quellen und Nachweise
- ORD-Eintrag
- ord-aeabfc772e984de0ab3083e18055c31a
- Quelldatensatz
- uspto-grants-2015_07
- Patentnummer
- US09073894B2
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