Potassium Iodide → Ammonia

HRID 1433274ノート

反応式

HRID 1433274 の反応式
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:40]=[CH:41][CH:42]=1)[O:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:14]([C@@H:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH:15]=1.[I-].[K+].C(=O)([O-])O.[Na+].[CH2:50]([O:57][C:58]1[CH:63]=[CH:62][C:61]([C@@H:64]([O:67][Si:68]([C:71]([CH3:74])([CH3:73])[CH3:72])([CH3:70])[CH3:69])[CH2:65]Br)=[CH:60][C:59]=1[CH2:75][OH:76])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C(#N)CC.C(OCC)(=O)C.O>[NH3:1].[CH2:50]([O:57][C:58]1[CH:63]=[CH:62][C:61]([C@@H:64]([O:67][Si:68]([C:71]([CH3:73])([CH3:72])[CH3:74])([CH3:69])[CH3:70])[CH2:65][NH:1][CH2:2][CH2:3][C:4]2[CH:42]=[CH:41][CH:40]=[C:6]([O:7][CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:14]([C@@H:16]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:17][CH2:18][N:19]([CH:20]([CH3:22])[CH3:21])[CH:23]([CH3:25])[CH3:24])[CH:15]=3)[CH:5]=2)=[CH:60][C:59]=1[CH2:75][OH:76])[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

参加物

9

反応物 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 12988834[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanolHCID 57933181(3R)-3-[5-{2-[3-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

生成物 2

HCID 222AmmoniaHCID 57933183{2-(benzyloxy)-5-[(1R)-2-({2-[3-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanol

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 7854Propionitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(3R)-3-[5-{2-[3-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Preparation 38, 470 mg, 0.72 mmol), potassium iodide (120 mg, 0.72 mmol), sodium hydrogen carbonate (240 mg, 2.9 mmol) and {2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanol (Prepared according to WO2004/032921, 325 mg, 0.72 mmol) were stirred in propionitrile at 100° C. for 24 hours under nitrogen. After cooling to room temperature, water (100 ml) and ethyl acetate (100 ml) were added, organics separated and washed with brine (100 ml), dried (magnesium sulphate) and solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (100/0/0 to 8511511.5 by volume) to furnish the title compound as a brown glass, 450 mg.

後処理

  1. customorganics separated
  2. washwashed with brine (100 ml)
  3. dry with materialdried (magnesium sulphate) and solvent
  4. customremoved 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-6ac37655c58748ea9bad700efd1fa687
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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