Sodium Carbonate → Abiraterone Acetate

HRID 525310

Reaktionsgleichung

Reaktionsgleichung von HRID 525310
O(C=C)S(C(F)(F)F)(=O)=O.C(B(CC)[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)C.FC(F)(F)S(O[C:28]1[C@:29]2([CH2:46][CH2:45][C@H:44]3[C@@H:34]([CH2:35][CH:36]=[C:37]4[C@:42]3([CH3:43])[CH2:41][CH2:40][C@H:39]([O:47][C:48](=[O:50])[CH3:49])[CH2:38]4)[C@@H:31]2[CH2:32][CH:33]=1)[CH3:30])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C.O1CCCC1>[CH3:49][C:48]([O:47][C@@H:39]1[CH2:38][C:37]2[C@@:42]([CH3:43])([C@@H:44]3[C@@H:34]([CH2:35][CH:36]=2)[C@@H:31]2[CH2:32][CH:33]=[C:28]([C:14]4[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=4)[C@@:29]2([CH3:30])[CH2:46][CH2:45]3)[CH2:41][CH2:40]1)=[O:50]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 10457059((3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(trifluoromethylsulfonyloxy)-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta(a)phenanthren-3-yl) acetateHCID 11769071Vinyl triflate

Produkt 1

HCID 9821849Abiraterone Acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Trifluoromethanesulphonic anhydride (235 g) is dropped into a solution of prasterone acetate (250 g) in methylene chloride (5 L), maintaining the temperature between −5° C. and 0° C., and anhydrous sodium carbonate (80 g) is added in portions. The mixture is stirred for 4 h at 0-5° C. Cold water (2.5 L) is added and the organic phase is separated and washed with a 10% sodium chloride aqueous solution. The mixture is treated with decolourising carbon (120 g), and then concentrated under vacuum to obtain an oily residue (about 355 g). The vinyl triflate thus obtained is taken up with tetrahydrofuran (3.0 L), and diethyl(3-pyridyl)borane (100 g), bis(triphenylphosphine)palladium II chloride (3.3 g) and a 2M sodium carbonate aqueous solution (900 mL) are loaded in succession in an inert gas environment. The resulting mixture is refluxed for about 1 h, then cooled to room temperature, and ethyl acetate (2.5 L) and water (2.5 L) are added. The aqueous phase is back-extracted with ethyl acetate (1.4 L), and the combined organic phases are treated with decolourising carbon (about 100 g), and then concentrated under vacuum to obtain crude abiraterone acetate as an oil (304 g; purity about 92%; assay 52%).

Aufarbeitung

  1. temperatureThe resulting mixture is refluxed for about 1 h
  2. extractionThe aqueous phase is back-extracted with ethyl acetate (1.4 L)
  3. additionthe combined organic phases are treated with decolourising carbon (about 100 g)
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-424e83cee79449e3bdf3ea5ea5035615
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340571B2

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