Methanol → Abiraterone Acetate

HRID 630372Notes

Reaction equation

HRID 630372 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][C@@:9]12[C@H:18]3[CH2:19][CH2:20][C@:21]4([CH3:32])[C:25]([C:26]5[CH:27]=[CH:28][CH:29]=[N:30][CH:31]=5)=[CH:24][CH2:23][C@H:22]4[C@@H:17]3[CH2:16][CH:15]=[C:14]1[CH2:13][C@@H](O)C[CH2:10]2.CO.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[CH3:6][C:5]([O:4][C@@H:1]1[CH2:13][C:14]2[C@@:9]([CH3:10])([C@@H:18]3[C@@H:17]([CH2:16][CH:15]=2)[C@@H:22]2[CH2:23][CH:24]=[C:25]([C:26]4[CH:27]=[CH:28][CH:29]=[N:30][CH:31]=4)[C@@:21]2([CH3:32])[CH2:20][CH2:19]3)[CH2:8][CH2:2]1)=[O:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 132971Abiraterone

Product 1

HCID 9821849Abiraterone Acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
70 °C

Procedure

Acetic anhydride (70 g) is added to a suspension of Abiraterone (16 g) in ethyl acetate (48 mL) The mixture is heated to 70° C. until the reaction is complete (about 20 h); the temperature is then reduced to about 50° C. and methanol (28 mL) is added. The resulting mixture is maintained under stirring for 2 h, cooled to room temperature, and ethyl acetate (110 mL) and an aqueous solution of sodium carbonate (450 mL) are added. The phases are separated and the organic phase is treated with decolourising carbon. The organic phase is then concentrated under vacuum and the concentrate is taken up with acetonitrile (about 80 mL) to obtain a sandy solid, which is isolated by filtration (at 0-5° C.) and dried under vacuum at 40° C. for 8 h (about 15 g).

Workup

  1. custom(about 20 h)
  2. customis then reduced to about 50° C.
  3. temperatureThe resulting mixture is maintained
  4. temperaturecooled to room temperature
  5. customThe phases are separated
  6. additionthe organic phase is treated with decolourising carbon
  7. concentrationThe organic phase is then concentrated under vacuum
  8. customto obtain a sandy solid
  9. customwhich is isolated by filtration (at 0-5° C.)
  10. customdried under vacuum at 40° C. for 8 h (about 15 g)

Sources & evidence

ORD record
ord-b9a79797034d4efdbd42f595d1b0a9a5
Source dataset
uspto-grants-2016_04
Patent number
US09315541B2

Reaction notes

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