Phenol → 4-((2s)-2-Hydroxy-3-{[1-(4-methoxy-benzenesulfonyl)-piperidin-4-ylmethyl]-amino}-propoxy)-phenol

HRID 1634790ノート

反応式

HRID 1634790 の反応式
C([Si]([O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@@H:27]2[CH2:29][O:28]2)=[CH:21][CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.NCC1CCN([C:38]2[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:39]=2[S:46]([NH2:49])(=[O:48])=[O:47])CC1.[C:50]1(O)[CH:55]=[CH:54][CH:53]=[CH:52]C=1.CCC[CH2:60][N+:61](CCCC)(CCCC)CCCC.[F-]>CO.C1COCC1>[OH:28][C@@H:27]([CH2:29][NH:61][CH2:60][CH:54]1[CH2:53][CH2:52][N:49]([S:46]([C:39]2[CH:38]=[CH:43][C:42]([O:44][CH3:45])=[CH:41][CH:40]=2)(=[O:47])=[O:48])[CH2:50][CH2:55]1)[CH2:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([OH:18])=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 996PhenolHCID 2724141Tetrabutylammonium FluorideHCID 11327180t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilaneHCID 18678703HCID 18678703、化合物

生成物 1

HCID 102258704-((2s)-2-Hydroxy-3-{[1-(4-methoxy-benzenesulfonyl)-piperidin-4-ylmethyl]-amino}-propoxy)-phenol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilane (0.078 g, 0.19 mmol) and an excess of and (4-aminomethyl-1-piperidinyl)-4-methoxybenzene-sulfonamide (0.109 g, 0.38 mmol) was heated as a solution in methanol at 60° C. for 24 hours. The reaction mixture was preabsorbed on silica gel and purified by flash chromatography (CH2Cl2—CH3OH, 19:1) to give the intermediate silyl-protected product. Deprotection to the phenol was accomplished by treatment of the silyl intermediate with 1M TBAF in THF. After stirring 15 minutes the solvent was evaporated and the product isolated by flash chromatography (CH2Cl2—CH3OH, 12:1) to give 0.049 g of the title compound as a white solid.

後処理

  1. customThe reaction mixture was preabsorbed on silica gel
  2. custompurified by flash chromatography (CH2Cl2—CH3OH, 19:1)
  3. customto give the intermediate silyl-
  4. customwas evaporated
  5. customthe product isolated by flash chromatography (CH2Cl2—CH3OH, 12:1)

出典と根拠

ORDレコード
ord-b916ab1570e34d02b5f3d20c2f717364
出典データセット
uspto-grants-2003_01
特許番号
US06506901B2

反応ノート

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