Water → 17beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3-benzyloxy-5-(3-(benzyloxycarbonyl)propoxy)phenyl)propyl)-5alpha-androstan-3-one

HRID 1744794노트

반응식

HRID 1744794 반응식
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([CH2:19][C:20](=[O:28])[CH2:21][CH2:22]1)[CH2:17][C@H:16]3[CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[C:36]([OH:38])[CH:35]=[C:34]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:33]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH2:49]([O:56][C:57](=[O:62])[CH2:58][CH2:59][CH2:60]Br)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.O>CN(C=O)C>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([CH2:19][C:20](=[O:28])[CH2:21][CH2:22]1)[CH2:17][C@H:16]3[CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[C:36]([O:38][CH2:60][CH2:59][CH2:58][C:57]([O:56][CH2:49][C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)=[O:62])[CH:35]=[C:34]([O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:33]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3832489Benzyl 4-bromobutanoateHCID 6962670717beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3-benzyloxy-5-hydroxyphenyl)propyl)-5alpha-androstan-3-one

생성물 1

HCID 6962690117beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3-benzyloxy-5-(3-(benzyloxycarbonyl)propoxy)phenyl)propyl)-5alpha-androstan-3-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 17β-(tert-butyldimethylsilyloxy)-7α-(3-(3-benzyloxy-5-hydroxyphenyl)propyl)-5α-androstan-3-one (21.0 mg) in DMF (0.3 ml) was cooled on ice, followed by addition of sodium hydride (1.6 mg) and 15-crown-5-ether (7.8 μl). After the reaction mixture was stirred for 30 minutes, 4-bromo-n-butyric acid benzyl ester (10 mg) was added and stirred on ice for 1 hour. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then filtered. After evaporation under reduced pressure to remove the solvent, the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/4) to give 17β-(tert-butyldimethylsilyloxy)-7α-(3-(3-benzyloxy-5-(3-(benzyloxycarbonyl)propoxy)phenyl)propyl)-5α-androstan-3-one.

후처리

  1. stirringstirred on ice for 1 hour
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customAfter evaporation under reduced pressure
  7. customto remove the solvent
  8. customthe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/4)

출처 및 근거

ORD 기록
ord-c6387fcf6b43481a82ad554483a5229d
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07018993B2

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