Water → HCID 53711472, Verbindung

HRID 1684567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684567
Cl([O-])=O.[Na+].[F:5][C:6]([F:34])([F:33])[CH2:7][CH2:8][CH2:9][C:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:28]([CH2:29][CH2:30][C@:13]12[CH3:14])[C@:26]1([CH3:27])[C:21]([CH:22]=[C:23]([CH:31]=[O:32])[CH2:24][CH2:25]1)=[CH:20][CH2:19]3)=[O:11].P([O-])([O-])([O-])=[O:36].[Na+].[Na+].[Na+].O>CC(=CC)C.C1COCC1.C(O)(=O)C.C(O)(C)(C)C>[F:5][C:6]([F:33])([F:34])[CH2:7][CH2:8][CH2:9][C:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:28]([CH2:29][CH2:30][C@:13]12[CH3:14])[C@:26]1([CH3:27])[C:21]([CH:22]=[C:23]([C:31]([OH:36])=[O:32])[CH2:24][CH2:25]1)=[CH:20][CH2:19]3)=[O:11]

Komponenten

9

Edukt 4

HCID 962WaterHCID 24243Trisodium PhosphateHCID 22874155HCID 22874155, VerbindungHCID 23668197Sodium Chlorite

Produkt 1

HCID 53711472HCID 53711472, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 105532-Methyl-2-buteneLösungsmittel

Versuchsvorschrift

Sodium chlorite (53 mg, 0.6 mmol) was added to a mixture of 17β-(5,5,5-trifluoro-1-oxopentyl)-androsta-3,5-diene-3-carboxaldehyde (50 mg, 0.12 mmol), sodium phosphate, monobasic monohydrate (140 mg, 1.18 mmol) in 2-methyl-2-butene in THF (2.0M, 3.0 ml), H2O (0.5 mL), and t-butanol (0.5 ml) at RT. After 6 h acetic acid (3.0 mL) was added, then the aqueous layer was extracted with EtOAc (10 mL), the combined organic extracts were dried (MgSO4), filtered, concentrated, and flash chromatographed (silica gel, 1% AcOH/19% EtOAc/80% hexanes) to yield the title compound as a white waxy solid. ESMS m/e 439 [M+H]+

Aufarbeitung

  1. customat RT
  2. extractionthe aqueous layer was extracted with EtOAc (10 mL)
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customflash chromatographed (silica gel, 1% AcOH/19% EtOAc/80% hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f4de43ed66cd41a180881bcacaca84e4
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05641765

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