化工社化工社 化学情報印刷レポート · 研究参考用
Sodium Carbonate → Abiraterone Acetate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | 3beta-Acetoxyandrost-5-en-17-one | HCID 14709 | — |
| 反応物 | 3-(Diethylboryl)pyridine | HCID 642851 | — |
| 反応物 | ((3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(trifluoromethylsulfonyloxy)-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta(a)phenanthren-3-yl) acetate | HCID 10457059 | — |
| 反応物 | Vinyl triflate | HCID 11769071 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | Abiraterone Acetate | HCID 9821849 | — |
反応手順
The crude vinyl triflate thus obtained (about a 4:1 mixture of vinyl triflate and prasterone acetate) is taken up with tetrahydrofuran (3.7 L). Diethyl(3-pyridyl)borane (90 g), bis(triphenylphosphine)palladium II chloride (3.8 g) and a 2M sodium carbonate aqueous solution (1 L) are loaded under inert gas environment. The resulting mixture is refluxed for about 1 h, then cooled to room temperature, and ethyl acetate (2.5 L) and water (2.5 L) are added. The aqueous phase is back-extracted with ethyl acetate (1.4 L), the combined organic phases are treated with decolourising carbon (about 100 g), and then concentrated under vacuum to obtain crude abiraterone acetate as an oil (320 g; purity about 87%; assay 51%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09340571B2 |
| 出典データセット | uspto-grants-2016_05 |
| ORD ID | ord-d7acb025435c4a3f91b314e9a17092be |
| 出典メモ | uspto-grants-2016_05 |