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Potassium Iodide → Ammonia

HRID 1433257
ノート
印刷プレビュー

反応式

HRID 1433257 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-77129ac189504749a7eb9a365d0d7ae3
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07612084B2

反応ノート

読み込み中…

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