Diisopropylethylamine → 11beta-Fluoro-7alpha-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}estra-1,3,5(10)-trien-3-ol-17-one

HRID 493900노트

반응식

HRID 493900 반응식
C(N(C(C)C)C(C)C)C.[F:10][C@H:11]1[CH2:28][C@@:26]2([CH3:27])[C@@H:22]([CH2:23][CH2:24][C@@H:25]2[OH:29])[C@H:21]2[C@H:12]1[C:13]1[CH:14]=[CH:15][C:16]([OH:56])=[CH:17][C:18]=1[CH2:19][C@H:20]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]([CH3:55])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([F:54])([F:53])[C:43]([F:52])([F:51])[C:44]([F:50])([F:49])[C:45]([F:48])([F:47])[F:46]>CS(C)=O.C(OCC)(=O)C>[F:10][C@H:11]1[CH2:28][C@@:26]2([CH3:27])[C@@H:22]([CH2:23][CH2:24][C:25]2=[O:29])[C@H:21]2[C@H:12]1[C:13]1[CH:14]=[CH:15][C:16]([OH:56])=[CH:17][C:18]=1[CH2:19][C@H:20]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]([CH3:55])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([F:53])([F:54])[C:43]([F:51])([F:52])[C:44]([F:49])([F:50])[C:45]([F:46])([F:47])[F:48]

참가 물질

5

반응물 2

HCID 81531DiisopropylethylamineHCID 1585865411beta-Fluoro-7alpha-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}-estra-1,3,5(10)-triene-3,17beta-diol

생성물 1

HCID 1209588811beta-Fluoro-7alpha-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}estra-1,3,5(10)-trien-3-ol-17-one

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 8857Ethyl Acetate용매

실험 절차

1.5 ml of ethyldiisopropylamine is added in drops at 10° C. to a solution of 1.23 g of pyridine sulfur trioxide complex in 10 ml of dried dimethyl sulfoxide. Then, 1.72 g of 11β-fluoro-7α-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}-estra-1,3,5(10)-triene-3,17β-diol (compound No. Z9) as well as another 10 ml of dried dimethyl sulfoxide are added and stirred for 30 minutes at room temperature. Then, it is diluted with ethyl acetate, washed with saturated sodium bicarbonate solution, water and sodium chloride solution, dried on sodium sulfate, evaporated to the dry state in a vacuum and chromatographed on silica gel with dichloromethane/methanol. 11β-Fluoro-7α-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl} estra-1,3,5(10)-trien-3-ol-17-one, [α]D=+58.2°, in chloroform, is obtained.

후처리

  1. washwashed with saturated sodium bicarbonate solution, water and sodium chloride solution
  2. customdried on sodium sulfate
  3. customevaporated to the dry state in a vacuum
  4. customchromatographed on silica gel with dichloromethane/methanol

출처 및 근거

ORD 기록
ord-6b2e01daa1b94151b202a71c96e250d0
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538100B2

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