Acetyl chloride → Abiraterone Acetate

HRID 1451373Notes

Reaction equation

HRID 1451373 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) containing 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 white 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-6890e315eb5645129ab03e396119e24c
Source dataset
uspto-grants-1997_02
Patent number
US05604213

Reaction notes

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