Sodium Bicarbonate → [(3S,8R,9S,10R,13S,14S)-7-methoxy-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate

HRID 551836ノート

反応式

HRID 551836 の反応式
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C@@H:9](Br)[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)(=[O:3])[CH3:2].[C:26](=O)(O)[O-:27].[Na+]>CO>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH:9]([O:27][CH3:26])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 11811651HCID 11811651、化合物

生成物 1

HCID 45092570[(3S,8R,9S,10R,13S,14S)-7-methoxy-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a clear solution of 3β-acetoxy-7α-bromoandrost-5-ene-17-one, 25, (0.5 g) in methanol (20 mL) was added silica gel (2.0 g, 70-230 mesh) and the mixture was stirred for 2 h at room temperature. The methanolic solution was cooled, neutralized with saturated sodium bicarbonate solution, and filtered on a thin bed of celite. The clear filtrate was cooled at 0° C. to obtain the white crystalline 7-methoxy derivative 26. Yield 0.32 g (72.7%), m.p. 175-78° C. The NMR spectrum of the white solid showed 55% 7β-methoxy- and 45% 7α-methoxy-compound. Spectral data described below were deduced from the spectrum of the mixture. The biological activity was assayed as the mixture (Table I).

後処理

  1. temperatureThe methanolic solution was cooled
  2. filtrationfiltered on a thin bed of celite
  3. temperatureThe clear filtrate was cooled at 0° C.

出典と根拠

ORDレコード
ord-659e759f54d944f7bcdb3865f3b9d107
出典データセット
uspto-grants-2011_05
特許番号
US07947846B2

反応ノート

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