Sodium Carbonate → Abiraterone Acetate

HRID 525308

反応式

HRID 525308 の反応式
O(C=C)S(C(F)(F)F)(=O)=O.[CH3:11][C:12]([O:14][C@@H:15]1[CH2:28][C:27]2[C@@:18]([CH3:34])([C@@H:19]3[C@@H:24]([CH2:25][CH:26]=2)[C@@H:23]2[CH2:29][CH2:30][C:31](=O)[C@@:22]2([CH3:33])[CH2:21][CH2:20]3)[CH2:17][CH2:16]1)=[O:13].C(B(CC)[C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1)C.FC(F)(F)S(OC1[C@]2(CC[C@H]3[C@@H](CC=C4[C@]3(C)CC[C@H](OC(=O)C)C4)[C@@H]2CC=1)C)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C.O1CCCC1>[CH3:11][C:12]([O:14][C@@H:15]1[CH2:16][C:17]2[C@@:18]([CH3:34])([C@@H:19]3[C@@H:24]([CH2:25][CH:26]=2)[C@@H:23]2[CH2:29][CH:30]=[C:31]([C:42]4[CH:43]=[CH:38][CH:39]=[N:40][CH:41]=4)[C@@:22]2([CH3:33])[CH2:21][CH2:20]3)[CH2:27][CH2:28]1)=[O:13]

参加物

9

反応物 5

HCID 10340Sodium CarbonateHCID 147093beta-Acetoxyandrost-5-en-17-oneHCID 6428513-(Diethylboryl)pyridineHCID 10457059((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) acetateHCID 11769071Vinyl triflate2 回

生成物 1

HCID 9821849Abiraterone Acetate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  1. temperatureThe resulting mixture is refluxed for about 1 h
  2. extractionThe aqueous phase is back-extracted with ethyl acetate (1.4 L)
  3. additionthe combined organic phases are treated with decolourising carbon (about 100 g)
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-d7acb025435c4a3f91b314e9a17092be
出典データセット
uspto-grants-2016_05
特許番号
US09340571B2

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