Potassium Iodide → Ammonia

HRID 1433250ノート

反応式

HRID 1433250 の反応式
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[CH:39]=[CH:38][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C@@H:22]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:23][CH2:24][N:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH:16]=2)=[CH:8][CH:7]=1.[CH2:40]([O:47][C:48]1[CH:53]=[CH:52][C:51]([C@@H:54]([O:57][Si:58]([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59])[CH2:55]Br)=[CH:50][C:49]=1[NH:65][S:66]([CH3:69])(=[O:68])=[O:67])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])O.[Na+].[I-].[K+]>O.C(#N)C>[NH3:3].[CH2:40]([O:47][C:48]1[CH:53]=[CH:52][C:51]([C@@H:54]([O:57][Si:58]([C:61]([CH3:62])([CH3:64])[CH3:63])([CH3:60])[CH3:59])[CH2:55][NH:3][CH2:4][CH2:5][C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C@@H:22]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:23][CH2:24][N:25]([CH:26]([CH3:28])[CH3:27])[CH:29]([CH3:30])[CH3:31])[CH:16]=3)=[CH:38][CH:39]=2)=[CH:50][C:49]=1[NH:65][S:66]([CH3:69])(=[O:67])=[O:68])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

参加物

8

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 866164804-{4-[4-(2-Aminoethyl)phenoxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol bis hydrochloride salt

生成物 2

HCID 222AmmoniaHCID 57933232N-{2-(Benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]phenyl}methanesulfonamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

4-{4-[4-(2-aminoethyl)phenoxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol bis hydrochloride salt (Preparation 13, 420 mg, 0.73 mmol), N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 375 mg, 0.73 mmol), sodium hydrogen carbonate (245 mg, 2.92 mmol) and potassium iodide (121 mg, 0.73 mmol) were added to acetonitrile (15 ml) and heated to 90° C. for 30 minutes and left at room temperature for 48 hours, water was 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 (971310.3 to 92/810.8 by volume) to furnish the title compound as a white foam, 207 mg.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (magnesium sulphate)
  3. customthe solvent 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-cdee056ef52248b4bb45571a676bef36
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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