Acetic Anhydride → Abiraterone Acetate

HRID 525309

反応式

HRID 525309 の反応式
[CH3:1][C@@:2]12[C@H:11]3[CH2:12][CH2:13][C@:14]4([CH3:25])[C:18]([C:19]5[CH:20]=[CH:21][CH:22]=[N:23][CH:24]=5)=[CH:17][CH2:16][C@H:15]4[C@@H:10]3[CH2:9][CH:8]=[C:7]1[CH2:6][C@@H:5]([OH:26])[CH2:4][CH2:3]2.[C:27](OC(=O)C)(=[O:29])[CH3:28].C(N(CC)CC)C>C(Cl)Cl>[CH3:28][C:27]([O:26][C@@H:5]1[CH2:6][C:7]2[C@@:2]([CH3:1])([C@@H:11]3[C@@H:10]([CH2:9][CH:8]=2)[C@@H:15]2[CH2:16][CH:17]=[C:18]([C:19]4[CH:20]=[CH:21][CH:22]=[N:23][CH:24]=4)[C@@:14]2([CH3:25])[CH2:13][CH2:12]3)[CH2:3][CH2:4]1)=[O:29]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 132971Abiraterone

生成物 1

HCID 9821849Abiraterone Acetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-2.5 °C

実験手順

The crude abiraterone thus obtained (about 64 g) is taken up in methylene chloride (350 mL), and the resulting mixture, cooled to a temperature of −5 to 0° C., is added with acetic anhydride (130 mL) and then with triethylamine (190 mL), maintaining the temperature at −5 to 0° C. The mixture is stirred at room temperature for about 25 h, then washed with water and concentrated under vacuum, taking up the residue in acetone (250 mL). The resulting solid is isolated by filtration (at 0-5° C.) and dried under vacuum at 40° C. for 16 h (about 46 g; purity: 82.5%; assay: about 73%). A second fraction of crude abiraterone acetate, as an oil, is obtained by concentration of the mother liquor under vacuum (54 g, purity: 74%, assay: about 45%).

後処理

  1. washwashed with water
  2. concentrationconcentrated under vacuum
  3. customThe resulting solid is isolated by filtration (at 0-5° C.)
  4. customdried under vacuum at 40° C. for 16 h (about 46 g; purity: 82.5%; assay: about 73%)

出典と根拠

ORDレコード
ord-0907400267d446e097fd7a128ebf2ddc
出典データセット
uspto-grants-2016_05
特許番号
US09340571B2

関連ノート

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