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

HRID 1634790노트

반응식

HRID 1634790 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b916ab1570e34d02b5f3d20c2f717364
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506901B2

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