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Water → Ammonia

HRID 1433246
ノート
印刷プレビュー

反応式

HRID 1433246 の反応式
[NH2:1][CH2:2][CH2:3][C:4]1[CH:36]=[CH:35][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C@@H:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:20][CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:13]=2)=[CH:6][CH:5]=1.[CH2:37]([O:44][C:45]1[CH:50]=[CH:49][C:48]([C@@H:51]([O:54][Si:55]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56])[CH2:52]Br)=[CH:47][C:46]=1[NH:62][S:63]([CH3:66])(=[O:65])=[O:64])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(OCC)(=O)C.O>CS(C)=O>[NH3:1].[CH2:37]([O:44][C:45]1[CH:50]=[CH:49][C:48]([C@@H:51]([O:54][Si:55]([C:58]([CH3:59])([CH3:61])[CH3:60])([CH3:57])[CH3:56])[CH2:52][NH:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C@@H:19]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:20][CH2:21][N:22]([CH:26]([CH3:27])[CH3:28])[CH:23]([CH3:25])[CH3:24])[CH:13]=3)=[CH:35][CH:36]=2)=[CH:47][C:46]=1[NH:62][S:63]([CH3:66])(=[O:64])=[O:65])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=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 962WaterHCID 8857Ethyl AcetateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 579331574-{3-[4-(2-aminoethyl)phenoxy]propyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol

生成物 2

HCID 222Ammonia
HCID 57933186
N-{2-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}amino)ethyl]phenyl}methanesulfonamide

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

4-{3-[4-(2-aminoethyl)phenoxy]propyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol (Preparation 8, 134 mg, 0.27 mmol) and N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 145 mg, 0.28 mmol) were heated at 90° C. in dimethylsulfoxide (0.5 ml) for 24 hours. Ethyl acetate (20 ml) and water (10 ml) were added and the organics separated. The aqueous was washed with ethyl acetate (20 ml) and the combined organics washed with brine (10 ml), 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 (80/20/2.0 by volume) to furnish the title compound as a glass, 101 mg.

後処理

  1. washThe aqueous was washed with ethyl acetate (20 ml)
  2. washthe combined organics washed with brine (10 ml)
  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-1daf65f8d1054da6bbd27128ecc741bf
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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