Reaktion #618393

ord-15b89b14420741f79eae02e35ab6bc75

Reaktionsgleichung

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12
abiraterone
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(c4cccnc4)=CC[C@@H]32)C1
abiraterone acetate

Edukte

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12
abiraterone
CC(=O)OC(C)=O
acetic anhydride

Reagenzien

Keine

Lösungsmittel

CCN(CC)CC
triethylamine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigepurified in hexane

Vorschrift

In one embodiment of the invention, abiraterone is acetylated by using acetic anhydride in the presence of a base, preferably triethylamine, and purified in hexane and ethanol to give pure abiraterone acetate of formula (I) with an overall yield up to 43-45% from the DHEA and a high purity (up to 99.0% by HPLC). In this embodiment, charcoal and a chelating resin are advantageously added to the hexane and ethanol solution of abiraterone acetate; the reaction mixture is then filtered and the pure active ingredient is crystallized. Suitable chelating resins that can be used in the invention are immobilized resins such as complex phenol-formaldehyde based resins; the Hokuetsu brand type MA-A resin (available from Ajinomoto) being preferred.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09353145B2uspto-grants-2016_05