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 1882090ノート

反応式

HRID 1882090 の反応式
[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

参加物

5

反応物 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

生成物 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]methanol収率 63.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-81eada0ea6e04b2fb2dcdca15668ef4f
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

読み込み中…