Acetic Anhydride → Abiraterone Acetate

HRID 525309

반응식

HRID 525309 반응식
[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]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 132971Abiraterone

생성물 1

HCID 9821849Abiraterone Acetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-2.5 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-0907400267d446e097fd7a128ebf2ddc
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340571B2

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