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Water → Ammonia

HRID 1433241
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HRID 1433241 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])=[CH:11][C:10]=1[C@@H:26]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:27][CH2:28][N:29]([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:42]([O:49][C:50]1[CH:55]=[CH:54][C:53]([C@@H:56]([O:59][Si:60]([C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:62])[CH3:61])[CH2:57]Br)=[CH:52][C:51]=1[NH:67][S:68]([CH3:71])(=[O:70])=[O:69])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(OCC)(=O)C.O>CS(C)=O>[NH3:25].[CH2:42]([O:49][C:50]1[CH:55]=[CH:54][C:53]([C@@H:56]([O:59][Si:60]([C:63]([CH3:64])([CH3:66])[CH3:65])([CH3:62])[CH3:61])[CH2:57][NH:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]([C@@H:26]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:27][CH2:28][N:29]([CH:30]([CH3:32])[CH3:31])[CH:33]([CH3:34])[CH3:35])[CH:11]=2)=[CH:52][C:51]=1[NH:67][S:68]([CH3:71])(=[O:69])=[O:70])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=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 6893123410-{4-(Benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}dec-9-en-1-amine

생성물 2

HCID 222Ammonia
HCID 86616474
N-{2-(benzyloxy)-5-[(1R)-2-{[10-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}dec-9-en-1-yl]amino}-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

10-{4-(Benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}dec-9-en-1-amine (Preparation 3, 170 mg, 0.33 mmol) and N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 180 mg, 0.33 mmol) were heated at 90° C. in dimethylsulfoxide (0.5 ml) for 12 hours. Ethyl acetate (20 ml) and water (10 ml) were added and the organics separated, washed with water (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, 90 mg.

후처리

  1. washthe organics separated, washed with water (10 ml)
  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-198d5fd5251843668dfc186333ba0bbf
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612084B2

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