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Potassium Iodide → Ammonia

HRID 1433279
ノート
印刷プレビュー

反応式

HRID 1433279 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:16]Br)=[CH:11][C:10]=1[NH:26][CH:27]=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[NH2:31][CH2:32][CH2:33][C:34]1[CH:72]=[CH:71][C:37]([O:38][CH2:39][CH2:40][C:41]2[CH:42]=[CH:43][C:44]([O:63][CH2:64][C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[C:45]([C@@H:47]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[CH2:48][CH2:49][N:50]([CH:54]([CH3:56])[CH3:55])[CH:51]([CH3:53])[CH3:52])[CH:46]=2)=[CH:36][CH:35]=1.[I-].[K+].C(=O)([O-])O.[Na+].C(#N)CC>C(OCC)(=O)C.O>[NH3:26].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:16][NH:31][CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([O:38][CH2:39][CH2:40][C:41]3[CH:42]=[CH:43][C:44]([O:63][CH2:64][C:65]4[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=4)=[C:45]([C@@H:47]([C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[CH2:48][CH2:49][N:50]([CH:51]([CH3:53])[CH3:52])[CH:54]([CH3:56])[CH3:55])[CH:46]=3)=[CH:71][CH:72]=2)=[CH:11][C:10]=1[NH:26][CH:27]=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 4875Potassium IodideHCID 7854PropionitrileHCID 516892Sodium BicarbonateHCID 574610672-bromo-(R)-1-tert-butyldimethylsiloxy-1-(3-formamido-4-benzyloxyphenyl)ethaneHCID 86616485(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine bis hydrochloride salt

生成物 2

HCID 222
Ammonia
HCID 57933175N-{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}formamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}formamide (Prepared according to US2005/215590, 440 mg, 0.95 mmol) (3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine bis hydrochloride salt (Preparation 42, 600 mg, 0.95 mmol) potassium iodide (160 mg, 0.94 mmol), sodium hydrogen carbonate (480 mg, 5.65 mmol) were added to propionitrile (10 ml) and stirred at 100° C. under nitrogen for 24 hours. The mixture was cooled and water (75 ml) and ethyl acetate (75 ml) were added. Organics were separated and washed with brine, 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 (99/1/0.1 to 90/10/1 by volume) to furnish the title compound as a gum, 174 mg.

後処理

  1. temperatureThe mixture was cooled
  2. customOrganics were separated
  3. washwashed with brine
  4. dry with materialdried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

出典と根拠

ORDレコード
ord-074cbe60fc8a4abc95396fa28f06156a
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…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート