Dimethyl Sulfoxide → HCID 25206537、化合物

HRID 562933

反応式

HRID 562933 の反応式
[OH:1][CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1.CS(C)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(N(CC)CC)C>C(Cl)Cl>[O:1]=[C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 14812Phosphorus oxide (P4O10)HCID 469110415-[4-(2-Hydroxy-2-phenylethoxy)benzyl]-1,3-thiazolidine-2,4-dione

生成物 1

HCID 25206537HCID 25206537、化合物収率 40.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirring solution of 5-[4-(2-hydroxy-2-phenylethoxy)benzyl]-1,3-thiazolidine-2,4-dione (1.00 g, 2.91 mmol) in DCM (35 ml) was added DMSO (2 ml) and the solution was cooled to 0° C. Phosphorus pentoxide (0.83 g, 2.91 mmol) was added followed by triethylamine (1.8 mL, 13.1 mmol). The reaction was allowed to slowly warm to RT. After 2 hours, the reaction mixture was partitioned between DCM and water and the organic phase was washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting yellow oil was chromatographed on silica gel eluting with 25-35% EtOAc/hexanes. Fractions containing product were combined and evaporated in vacuo to give 0.40 g (40%) of the title compound as a white solid. Trituration with ether afforded 245 mg of clean product. MS (ESI−) for C18H15NO4S m/z 340.1 (M−H)−.

後処理

  1. temperatureto slowly warm to RT
  2. customthe reaction mixture was partitioned between DCM and water
  3. washthe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting yellow oil was chromatographed on silica gel eluting with 25-35% EtOAc/hexanes
  8. additionFractions containing product
  9. customevaporated in vacuo

出典と根拠

ORDレコード
ord-4de34d84325b4729af7179bfe95e3cf7
出典データセット
uspto-grants-2011_11
特許番号
US08067450B2

関連ノート

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