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Potassium Iodide → Ammonia

HRID 1433257
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HRID 1433257 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[CH:42]=[CH:41][C:7]([O:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:15]([C@@H:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:16]=2)=[CH:6][CH:5]=1.[CH2:43]([O:50][C:51]1[CH:56]=[CH:55][C:54]([C@@H:57]([O:60][Si:61]([C:64]([CH3:67])([CH3:66])[CH3:65])([CH3:63])[CH3:62])[CH2:58]Br)=[CH:53][C:52]=1[NH:68][S:69]([CH3:72])(=[O:71])=[O:70])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(=O)([O-])O.[Na+].[I-].[K+]>C(#N)C>[NH3:1].[CH2:43]([O:50][C:51]1[CH:56]=[CH:55][C:54]([C@@H:57]([O:60][Si:61]([C:64]([CH3:65])([CH3:67])[CH3:66])([CH3:63])[CH3:62])[CH2:58][NH:1][CH2:2][CH2:3][C:4]2[CH:42]=[CH:41][C:7]([O:8][CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][C:14]([O:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[C:15]([C@@H:17]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:16]=3)=[CH:6][CH:5]=2)=[CH:53][C:52]=1[NH:68][S:69]([CH3:72])(=[O:70])=[O:71])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 57933208(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

생성물 2

HCID 222Ammonia
HCID 57933234
N-{2-(benzyloxy)-5-[(1R)-2-({2-[4-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Preparation 21, 95 mg, 0.17 mmol), N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (WO2005/080324, 86 mg, 0.17 mmol), sodium hydrogen carbonate (42 mg, 0.51 mmol) and potassium iodide (28 mg, 0.17 mmol) were added to acetonitrile (2.5 ml) and heated to reflux for 24 hours, then cooled to room temperature and the solvents removed in vacuo, the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (2421810.8 to 95/5/0.5 by volume) to furnish the title compound as a white foam, 78 mg.

후처리

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. customthe solvents removed in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-77129ac189504749a7eb9a365d0d7ae3
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612084B2

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