Potassium Iodide → Ammonia

HRID 1433254ノート

反応式

HRID 1433254 の反応式
Cl.Cl.[CH2:3]([O:10][C:11]1[CH:25]=[CH:24][C:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])=[CH:13][C:12]=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:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=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(=O)([O-])O.[Na+].[I-].[K+]>[Cl-].[Na+].O.O.C(#N)C>[NH3:23].[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:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:14]2[CH:24]=[CH:25][C:11]([O:10][CH2:3][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)=[C:12]([C@@H:26]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:27][CH2:28][N:29]([CH:33]([CH3:34])[CH3:35])[CH:30]([CH3:32])[CH3:31])[CH:13]=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

参加物

9

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 866164817-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptan-1-amine bis hydrochloride salt

生成物 2

HCID 222AmmoniaHCID 57933197N-{2-(Benzyloxy)-5-[(1R)-2-[(7-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
90 °C

実験手順

7-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptan-1-amine bis hydrochloride salt (Preparation 18, 190 mg, 0.31 mmol), N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 161 mg, 0.32 mmol), sodium hydrogen carbonate (106 mg, 1.26 mmol) and potassium iodide (52 mg, 0.32 mmol) were added to acetonitrile (5 ml) and heated to 90° C. for 24 hours, then left at room temperature over night, water and brine were added and extracted with ethyl acetate, 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 (98/2/0.2 to 92/8/0.8 by volume) to furnish the title compound as a colourless gum, 100 mg.

後処理

  1. waitleft at room temperature over night
  2. extractionextracted with ethyl acetate
  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

出典と根拠

ORDレコード
ord-acf33986388b46c0a96c432668f54562
出典データセット
uspto-grants-2009_11
特許番号
US07612084B2

反応ノート

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