Acetyl chloride → Abiraterone Acetate

HRID 53190

反応式

HRID 53190 の反応式
[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]

参加物

7

反応物 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 132971AbirateroneHCID 12698378Triethylazanium chloride

生成物 1

HCID 9821849Abiraterone Acetate収率 84.3%

試薬・触媒・溶媒 2

HCID 218852-Dimethylaminopyridine触媒HCID 3283Diethyl Ether溶媒

実験手順

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) coning 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 whim 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%).

後処理

  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)

出典と根拠

ORDレコード
ord-94d92c56bf574920853a00aa70205454
出典データセット
uspto-grants-1997_04
特許番号
US05618807

関連ノート

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