Acetyl chloride → Abiraterone Acetate

HRID 53190

Reaktionsgleichung

Reaktionsgleichung von HRID 53190
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C@:8]3([CH2:25][CH2:24][C@H:23]4[C@@H:13]([CH2:14][CH:15]=[C:16]5[C@:21]4([CH3:22])[CH2:20][CH2:19][C@H:18]([OH:26])[CH2:17]5)[C@@H:10]3[CH2:11][CH:12]=2)[CH3:9])[CH:2]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35].[Cl-].C([NH+](CC)CC)C>C(OCC)C.CN(C1C=CC=CN=1)C>[C:34]([O:26][C@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C:16](=[CH:15][CH2:14][C@@H:13]3[C@@H:23]2[CH2:24][CH2:25][C@@:8]2([CH3:9])[C@H:10]3[CH2:11][CH:12]=[C:7]2[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:17]1)(=[O:36])[CH3:35]

Komponenten

7

Edukt 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 132971AbirateroneHCID 12698378Triethylazanium chloride

Produkt 1

HCID 9821849Abiraterone AcetateAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 218852-DimethylaminopyridineKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a stirred suspension of finely powdered 17-(3-pyridyl)androsta-5,16-dien-3β-ol (3.50 g, 10 mmol) in dry diethyl ether (150 ml) coning triethylamine (2,3 ml, 16 mmol) and dimethylaminopyridine (0.012 g, 0.1 mmol) was added acetyl chloride (1.0 ml, 14 mmol). The mixture was then stirred at ambient temperature for 12 h, over which time a thick whim precipitate of triethylammonium chloride had formed. The mixture was then filtered and the filtrate concentrated to afford the crude product which was recrystallised firstly from ethanol/water (1:1), then finally from hexane to afford the title compound (3.30 g, 84%).

Aufarbeitung

  1. customhad formed
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate concentrated
  4. customto afford the crude product which
  5. customwas recrystallised firstly from ethanol/water (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-94d92c56bf574920853a00aa70205454
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618807

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