Potassium Hydroxide → Galeterone

HRID 254185ノート

反応式

HRID 254185 の反応式
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH:13]=[C:14]2[N:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]=[CH:25]2)[CH2:6]1)(=O)C.[OH-].[K+]>CO>[OH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH:13]=[C:14]2[N:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]=[CH:25]2)[CH2:6]1

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 11464592(3S,8R,9S,10R,13S,14S)-17-(1H-Benzo[D]imidazol-1-YL)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[A]phenanthren-3-YL acetate

生成物 1

HCID 11188409Galeterone収率 94%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The acetate 4 (1.3 g 3.02 mmol) was dissolved in methanol (20 mL) under an inert Ar atmosphere, and the resulting solution treated with 10% methanolic KOH (8 mL). The mixture was stirred at room temperature for 1.5 h, and then concentrated under reduced pressure at approx. 40° C. to a volume of 10 mL. This solution was poured into ice water (300 mL), and the resulting white precipitate was filtered, washed with water and dried. Crystallization from EtOAc/MeOH gave 5 (1.10 g, 94%), mp 189-190° C.; IR(CHCl3) 2934, 2339, 1609, 1490, 1453, 1291, 1040, 837, 808, 705, 663, 608, 578, 550, 517 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.02 (s, 3H, 18-CH3), 1.07 (s, 3H, 19-CH3), 3.55 (m, 1H, 3α-H), 5.41 (br s, 1H, 6-H), 5.99 (s, 1H, 16-H), 7.30 (m, 2H, aromatic-Hs), 7.54 (s, 1H, aromatic-H), 7.80 (s, 1H, aromatic-H), and 7.96 (s, 1H, 21-H). HRMS calcd 411.2407 (C26H32ON2.Na+). found 411.2396.

後処理

  1. concentrationconcentrated under reduced pressure at approx. 40° C. to a volume of 10 mL
  2. additionThis solution was poured into ice water (300 mL)
  3. filtrationthe resulting white precipitate was filtered
  4. washwashed with water
  5. customdried
  6. customCrystallization from EtOAc/MeOH

出典と根拠

ORDレコード
ord-28794f7a4fbb400890dda0a9a37e9953
出典データセット
uspto-grants-2011_01
特許番号
US07875599B2

反応ノート

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