Potassium Acetate → HCID 67270043, Verbindung

HRID 1695544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1695544
[OH:1][C@@H:2]1[C@H:15]2[C@@H:6]([CH2:7][CH2:8][C:9]3[C@:14]2([CH3:16])[CH2:13][CH:12]([CH:17]=O)[C:11](=O)[CH:10]=3)[C@@H:5]2[CH2:20][CH2:21][C@:22]3([C:26]4([CH2:30][O:29][CH2:28][O:27]4)[O:25][CH2:24][O:23]3)[C@@:4]2([CH3:31])[CH2:3]1.Cl.[F:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=1[NH:41][NH2:42].C([O-])(=O)C.[K+]>C(O)C.O>[F:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=1[N:41]1[C:11]2[CH:10]=[C:9]3[CH2:8][CH2:7][C@H:6]4[C@H:15]([C@:14]3([CH3:16])[CH2:13][C:12]=2[CH:17]=[N:42]1)[C@H:2]([OH:1])[CH2:3][C@@:4]1([CH3:31])[C@@:22]2([CH2:21][CH2:20][C@H:5]41)[C:26]1([CH2:30][O:29][CH2:28][O:27]1)[O:25][CH2:24][O:23]2

Komponenten

6

Edukt 3

HCID 517044Potassium AcetateHCID 27333012,4-Difluorophenylhydrazine hydrochlorideHCID 59810282HCID 59810282, Verbindung

Produkt 1

HCID 67270043HCID 67270043, VerbindungAusbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-10,13-dimethyl-3-oxo-1,2,3,6,7,8,9,10,11,12,13,14,15,16-tetradecahydrodispiro[cyclopenta[a]phenanthrene-17,4′-[1,3]dioxolane-5′,4″-[1,3]dioxolane]-2-carbaldehyde (Steroids 2003, (68), 177-191) (400 mg, 0.92 mmol) was dissolved in ethanol (10 ml) and water (1 ml). (2,4-difluorophenyl)hydrazine hydrochloride (167 mg, 0.92 mmol) and potassium acetate (160 mg, 1.63 mmol)) were added and the mixture was heated under microwave irradiation at 90° C. for 20 minutes. The mixture was partitioned between EtOAc (10 ml) and water (10 ml). The organic phase was washed with water (2 times 10 ml) and brine (5 ml) and was dried over Mg2SO4. Filtration followed by evaporation of the solvent gave 297 mg of the crude compound which was used as such without further purification. APCI-MS m/z: 541 [MH+].

Aufarbeitung

  1. customThe mixture was partitioned between EtOAc (10 ml) and water (10 ml)
  2. washThe organic phase was washed with water (2 times 10 ml) and brine (5 ml)
  3. dry with materialwas dried over Mg2SO4
  4. filtrationFiltration
  5. customfollowed by evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-8ae4b820b1984918af1cbdd14b8f880e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163724B2

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