Tetrabutylammonium Fluoride → [5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazol-2-yl]methanol

HRID 1882090노트

반응식

HRID 1882090 반응식
[Si]([O:18][CH2:19][C:20]1[S:21][C:22]([C:25]2[NH:26][C:27]([CH:30]([C:38]3[CH:43]=[CH:42][C:41]([S:44]([CH:47]4[CH2:49][CH2:48]4)(=[O:46])=[O:45])=[CH:40][CH:39]=3)[CH2:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:28][CH:29]=2)=[N:23][N:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH:47]1([S:44]([C:41]2[CH:42]=[CH:43][C:38]([CH:30]([C:27]3[NH:26][C:25]([C:22]4[S:21][C:20]([CH2:19][OH:18])=[N:24][N:23]=4)=[CH:29][CH:28]=3)[CH2:31][CH:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)=[CH:39][CH:40]=2)(=[O:45])=[O:46])[CH2:49][CH2:48]1

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 1361666602-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazole

생성물 1

HCID 136166657[5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazol-2-yl]methanol수율 63.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazole (122 mg) in tetrahydrofuran (1.2 mL) was added tetrabutylammonium fluoride (0.44 mL: 1M tetrahydrofuran solution), and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, and washed with saturated brine. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (51.3 mg, yield 63%) was obtained as white crystals from a fraction eluted with ethyl acetate-hexane (19:1, volume ratio). melting point 208.5-208.6° C. MS: 474 (MH+).

후처리

  1. washwashed with saturated brine
  2. dry with materialThe ethyl acetate layer was dried (MgSO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-81eada0ea6e04b2fb2dcdca15668ef4f
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

반응 노트

불러오는 중…