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Ethyl Acetate → Ammonia

HRID 1433286
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HRID 1433286 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([C@@H:17]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:11]=1.[CH2:33]([O:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([O:50][Si:51]([C:54]([CH3:57])([CH3:56])[CH3:55])([CH3:53])[CH3:52])[CH2:48]Br)=[CH:43][C:42]=1[NH:58][S:59]([CH3:62])(=[O:61])=[O:60])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>CS(C)=O>[NH3:1].[CH2:33]([O:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([O:50][Si:51]([C:54]([CH3:55])([CH3:57])[CH3:56])([CH3:53])[CH3:52])[CH2:48][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([C@@H:17]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:18][CH2:19][N:20]([CH:21]([CH3:23])[CH3:22])[CH:24]([CH3:25])[CH3:26])[CH:11]=2)=[CH:43][C:42]=1[NH:58][S:59]([CH3:62])(=[O:60])=[O:61])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 579331874-(8-aminooctyl)-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol

생성물 2

HCID 222Ammonia
HCID 57933228
N-[2-(benzyloxy)-5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(8-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}octyl)amino]ethyl}phenyl]methanesulfonamide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

4-(8-aminooctyl)-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol (Preparation 53, 170 mg, 0.39 mmol) and N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 191 mg, 0.37 mmol) were heated at 90° C. in dimethylsulfoxide (0.5 ml) overnight. Ethyl acetate and saturated aqueous sodium hydrogen carbonate were added and the organics separated, washed with saturated aqueous sodium hydrogen carbonate, brine, dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (99/1/0.1 to 95/5/0.5 by volume) to furnish the title compound as a yellow oil, 90 mg.

후처리

  1. washthe organics separated, washed with saturated aqueous sodium hydrogen carbonate, brine
  2. dry with materialdried (magnesium sulphate)
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-0ab038e0e3824f7ba8fe3aa7a7db2ec1
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612084B2

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