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Water → Ammonia

HRID 1433246
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HRID 1433246 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[CH:36]=[CH:35][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C@@H:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:20][CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:13]=2)=[CH:6][CH:5]=1.[CH2:37]([O:44][C:45]1[CH:50]=[CH:49][C:48]([C@@H:51]([O:54][Si:55]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56])[CH2:52]Br)=[CH:47][C:46]=1[NH:62][S:63]([CH3:66])(=[O:65])=[O:64])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(OCC)(=O)C.O>CS(C)=O>[NH3:1].[CH2:37]([O:44][C:45]1[CH:50]=[CH:49][C:48]([C@@H:51]([O:54][Si:55]([C:58]([CH3:59])([CH3:61])[CH3:60])([CH3:57])[CH3:56])[CH2:52][NH:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C@@H:19]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:20][CH2:21][N:22]([CH:26]([CH3:27])[CH3:28])[CH:23]([CH3:25])[CH3:24])[CH:13]=3)=[CH:35][CH:36]=2)=[CH:47][C:46]=1[NH:62][S:63]([CH3:66])(=[O:64])=[O:65])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 579331574-{3-[4-(2-aminoethyl)phenoxy]propyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol

생성물 2

HCID 222Ammonia
HCID 57933186
N-{2-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}amino)ethyl]phenyl}methanesulfonamide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

4-{3-[4-(2-aminoethyl)phenoxy]propyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol (Preparation 8, 134 mg, 0.27 mmol) and N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 145 mg, 0.28 mmol) were heated at 90° C. in dimethylsulfoxide (0.5 ml) for 24 hours. Ethyl acetate (20 ml) and water (10 ml) were added and the organics separated. The aqueous was washed with ethyl acetate (20 ml) and the combined organics washed with brine (10 ml), 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 (80/20/2.0 by volume) to furnish the title compound as a glass, 101 mg.

후처리

  1. washThe aqueous was washed with ethyl acetate (20 ml)
  2. washthe combined organics washed with brine (10 ml)
  3. dry with materialdried (magnesium sulphate)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-1daf65f8d1054da6bbd27128ecc741bf
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612084B2

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