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Nitric Acid → [(4aR,6R,8aS)-2-amino-8a-(2-fluoro-5-nitrophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-6-yl]methanol

HRID 217992
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 217992
S(=O)(=O)(O)O.[NH2:6][C:7]1[S:16][CH2:15][C@H:14]2[C@:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])([CH2:10][O:11][C@@H:12]([CH2:17][OH:18])[CH2:13]2)[N:8]=1.[N+:26]([O-])([OH:28])=[O:27].[OH-].[Na+]>C(O)(C(F)(F)F)=O>[NH2:6][C:7]1[S:16][CH2:15][C@H:14]2[C@:9]([C:19]3[CH:24]=[C:23]([N+:26]([O-:28])=[O:27])[CH:22]=[CH:21][C:20]=3[F:25])([CH2:10][O:11][C@@H:12]([CH2:17][OH:18])[CH2:13]2)[N:8]=1
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Komponenten

6

Edukt 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 58406040[(4aR,6R,8aS)-2-amino-8a-(2-fluorophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-6-yl]methanol

Produkt 1

HCID 58406109[(4aR,6R,8aS)-2-amino-8a-(2-fluoro-5-nitrophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-6-yl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Concentrated sulfuric acid (2.5 ml) was added dropwise to a solution of [(4aR,6R,8aS)-2-amino-8a-(2-fluorophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-6-yl]methanol (700 mg) in TFA (5 ml) in an ice bath. Then, fuming nitric acid (specific gravity: 1.52, 103 μl) was added dropwise at the same temperature, followed by stirring for one hour. The reaction mixture was poured into ice and made basic with a 5 N sodium hydroxide solution, followed by stirring at room temperature for two hours. The aqueous layer was extracted with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound (1.0 g).

Aufarbeitung

  1. additionThe reaction mixture was poured into ice
  2. stirringby stirring at room temperature for two hours
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-51bd7574f6784e3795a2d39b89ce72a5
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08198269B2

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