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Ethyl Acetate → Ammonia

HRID 1433286
ノート
印刷プレビュー

反応式

HRID 1433286 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([C@@H:17]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:11]=1.[CH2:33]([O:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([O:50][Si:51]([C:54]([CH3:57])([CH3:56])[CH3:55])([CH3:53])[CH3:52])[CH2:48]Br)=[CH:43][C:42]=1[NH:58][S:59]([CH3:62])(=[O:61])=[O:60])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>CS(C)=O>[NH3:1].[CH2:33]([O:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([O:50][Si:51]([C:54]([CH3:55])([CH3:57])[CH3:56])([CH3:53])[CH3:52])[CH2:48][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([C@@H:17]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:18][CH2:19][N:20]([CH:21]([CH3:23])[CH3:22])[CH:24]([CH3:25])[CH3:26])[CH:11]=2)=[CH:43][C:42]=1[NH:58][S:59]([CH3:62])(=[O:60])=[O:61])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 579331874-(8-aminooctyl)-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol

生成物 2

HCID 222Ammonia
HCID 57933228
N-[2-(benzyloxy)-5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(8-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}octyl)amino]ethyl}phenyl]methanesulfonamide

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

4-(8-aminooctyl)-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol (Preparation 53, 170 mg, 0.39 mmol) and N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 191 mg, 0.37 mmol) were heated at 90° C. in dimethylsulfoxide (0.5 ml) overnight. Ethyl acetate and saturated aqueous sodium hydrogen carbonate were added and the organics separated, washed with saturated aqueous sodium hydrogen carbonate, 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 95/5/0.5 by volume) to furnish the title compound as a yellow oil, 90 mg.

後処理

  1. washthe organics separated, washed with saturated aqueous sodium hydrogen carbonate, brine
  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-0ab038e0e3824f7ba8fe3aa7a7db2ec1
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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