Trifluoroacetic acid → 3-[6'-Hydroxymethyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

HRID 1928484ノート

反応式

HRID 1928484 の反応式
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:20]=[C:19]([C:21]3[CH:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)[CH:24]=[C:23]([CH2:37][O:38]C4CCCCO4)[N:22]=3)[CH:18]=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>[OH-].[Na+]>[OH:38][CH2:37][C:23]1[N:22]=[C:21]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:11]3[CH:10]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:14]=[CH:13][CH:12]=3)[N:20]=2)[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=2)[CH:24]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 68692639N-tert-butyl-3-[6'-(tetrahydro-pyran-2-yloxymethyl)-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

生成物 1

HCID 247602223-[6'-Hydroxymethyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide収率 23.4%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

反応条件

温度
23 °C

実験手順

To the above described N-tert-butyl-3-[6′-(tetrahydro-pyran-2-yloxymethyl)-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-benzenesulfonamide (0.550 g, 0.88 mmol) was added TFA (5 mL) and the reaction mixture was stirred at 23° C. for 18 h. The mixture was poured into 3 N NaOH-solution (100 ml) and stirred at 23° C. for 15 min, then partitioned between EtOAc and water, the organic layer was washed with saturated NaHCO3 solution and dried over MgSO4. Removal of the solvent in vacuum left a crude product which was triturated with diethyl ether to give the title compound as an off-white solid (0.100 g, 23%). MS (ISP) 486.0 [(M+H)+]; mp 213° C. (dec.).

後処理

  1. stirringstirred at 23° C. for 15 min
  2. custompartitioned between EtOAc and water
  3. washthe organic layer was washed with saturated NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent in vacuum
  6. waitleft a crude product which
  7. customwas triturated with diethyl ether

出典と根拠

ORDレコード
ord-b7e98097e55f4e109de33e7716e122e4
出典データセット
uspto-grants-2012_05
特許番号
US08183262B2

反応ノート

読み込み中…