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 551836노트

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HRID 551836 반응식
[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]

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 11811651HCID 11811651, 화합물

생성물 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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-659e759f54d944f7bcdb3865f3b9d107
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947846B2

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