Estrone → 3-Nicotinoyloxyestra-1,3,5(10)-trien-17-one

HRID 260197

반응식

HRID 260197 반응식
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH3:11][C@@:12]12[C:28](=[O:29])[CH2:27][CH2:26][C@H:25]1[C@H:24]1[C@@H:15]([C:16]3[CH:17]=[CH:18][C:19]([OH:30])=[CH:20][C:21]=3[CH2:22][CH2:23]1)[CH2:14][CH2:13]2>N1C=CC=CC=1>[C:2]([O:30][C:19]1[CH:18]=[CH:17][C:16]2[C@@H:15]3[C@H:24]([C@H:25]4[C@@:12]([CH2:13][CH2:14]3)([CH3:11])[C:28](=[O:29])[CH2:27][CH2:26]4)[CH2:23][CH2:22][C:21]=2[CH:20]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1

참가 물질

4

반응물 2

HCID 5870EstroneHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

생성물 1

HCID 137310683-Nicotinoyloxyestra-1,3,5(10)-trien-17-one

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To nicotinoyl chloride hydrochloride (2.65 g, 0.015 mol) in pyridine (20 ml) at 0° C. was added estrone (2 g, 0.0074 mol). The mixture was refluxed for one hour and then poured over 100 ml of ice cold water, filtered, and dried over P2O5 under vacuum. Yield 72% (2.0076 g), m.p. 207°-210° C. NMR (CDCl3) δ 9.3-9.1 (br s, 1H, C2 pyridinium proton), 8.8-8.6 (br d, 1H, C6 pyridinium proton, 8.4-8.2 (br d, 1H, C4 pyridinium proton), 7.5-7.1 (m, 2-H, C5 pyridinium proton+C1 estrone proton), 7.0-6.7 (m, 2H, C2,4 estrone protons), 3.2-1.3 (estrone skeletal protons, 15), 1.0-0.9 (s, 3H, C18 estrone protons). IR (KBr) 1750-1730 cm- 1 (broad C=O stretching). Anal. calculated for C24H25NO3 ; C, 76.76; H, 6.72; N, 3.73. Found: C, 76.37; H, 6.96; N, 3.67. The product is further characterized by the structural formula: ##STR1465##

후처리

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationfiltered
  3. dry with materialdried over P2O5 under vacuum

출처 및 근거

ORD 기록
ord-6883dc0c9a064b509d316d35a5b87655
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05525727

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