Acetyl chloride → Abiraterone Acetate

HRID 53190

Reaction equation

HRID 53190 reaction equation
[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]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 132971AbirateroneHCID 12698378Triethylazanium chloride

Product 1

HCID 9821849Abiraterone AcetateYield 84.3%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-94d92c56bf574920853a00aa70205454
Source dataset
uspto-grants-1997_04
Patent number
US05618807

Linked notes

Loading…