Hydrochloric Acid → Abiraterone

HRID 53180

Reaktionsgleichung

Reaktionsgleichung von HRID 53180
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH:13]=[C:14]2[C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:6]1)(=O)C.[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO.O>[N:26]1[CH:27]=[CH:28][CH:29]=[C:24]([C:14]2[C@:15]3([CH2:17][CH2:18][C@H:19]4[C@@H:10]([CH2:9][CH:8]=[C:7]5[C@:20]4([CH3:23])[CH2:21][CH2:22][C@H:5]([OH:4])[CH2:6]5)[C@@H:11]3[CH2:12][CH:13]=2)[CH3:16])[CH:25]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 9821849Abiraterone Acetate

Produkt 1

HCID 132971AbirateroneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3β-acetoxy-17-(3-pyridyl)androsta-5,16-diene (4.90g, 12.5 mmol) in methanol (50 ml) was added an aqueous solution of sodium hydroxide (10% w/v, 10 ml) and the mixture heated, with stirring, on an oil bath at 80° C. for 5 min., then allowed to cool. The mixture was poured into water, neutralised with hydrochloric acid (1M), rebasified with sainted sodium bicarbonate solution, and extracted with hot toluene (3×100 ml). The toluene extracts were combined, dried (Na2CO3), and concentrated. Chromatography, on elution with toluene-diethyl ether (2:1 ) afforded the title compound (3.45 g, 79%) which crystallised from toluene, mp 228°-229° C.; 1H-NMR (CDCl3 inter alia δ1.05(3H,s, 19-CH3), 1.07(3H,s,18-CH3), 3.54(1H,m,3α-H), 5.40(1H,dm,J 5.0 Hz, 6-H), 5.99(1H,m, 16-H), 7.22(1H,m,Py5-H), 7.65(1H,m,Py 4-H), 8.46(1H,m,Py 6H), 8.62(1H,m,Py 2-H), Anal. Calcd: C, 82.47; H, 8.94; N, 4.01. Found: C, 82.40; H, 8.91; N. 3.97%.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto cool
  3. extractionextracted with hot toluene (3×100 ml)
  4. dry with materialdried (Na2CO3)
  5. concentrationconcentrated
  6. washChromatography, on elution with toluene-diethyl ether (2:1 )

Quellen und Nachweise

ORD-Eintrag
ord-23b6b88dedb3456789c0f2f60f93a8e4
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618807

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