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Water → HCID 9886735, Verbindung

HRID 1937741
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1937741
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C@H:10]([OH:15])[C@@H:9]([NH:16][C:17](=[O:26])[C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=3)[C:8]=2[CH:27]=1)(=[O:3])[CH3:2].O.FC(F)(F)C(O)=[O:32].FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O>C(#N)C>[F:24][C:22]1[CH:23]=[C:18]([CH:19]=[C:20]([F:25])[CH:21]=1)[C:17]([NH:16][C@H:9]1[C:8]2[CH:27]=[C:4]([C:1](=[O:3])[CH2:2][OH:32])[CH:5]=[CH:6][C:7]=2[O:12][C:11]([CH3:14])([CH3:13])[C@@H:10]1[OH:15])=[O:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 170378Tidembersat

Produkt 1

HCID 9886735HCID 9886735, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

(3R,4S)-6-Acetyl-4-(3,5-difluorobenzamido)-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran D3 (1.88 g, 5.0 mmol) (Example 4 of WO95/34545) was dissolved in acetonitrile (25ml), water (5 ml) and trifluoroacetic acid (0.77 ml, 10.0 mmol). [Bis(trifluoroacetoxy)iodo]benzene (4.30 g, 10.0 mmol) was added and the reaction stirred under reflux for three hours. The reaction mixture was allowed to cool and the acetonitrile was removed in vacuo, the resulting material being partitioned between water (50 ml) and dichloromethane (125 ml). The aqueous layer was extracted with further portions of dichloromethane (3×25 ml) and the combined organic extracts were dried over magnesium sulphate, filtered and the solvent removed in vacuo. The resulting yellow solid was purified by column chromatography on silica, eluting with 20% to 40% ethyl acetate in hexane to afford the title compound as a white solid (0.70 g, 36%, m.p. 179.4° C.).

Aufarbeitung

  1. temperatureunder reflux for three hours
  2. temperatureto cool
  3. customthe acetonitrile was removed in vacuo
  4. customthe resulting material being partitioned between water (50 ml) and dichloromethane (125 ml)
  5. extractionThe aqueous layer was extracted with further portions of dichloromethane (3×25 ml)
  6. dry with materialthe combined organic extracts were dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe resulting yellow solid was purified by column chromatography on silica
  10. washeluting with 20% to 40% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-735a55d5d83d4290a4e1b986af91af95
Quelldatensatz
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06395909B1

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