Tetrabutylammonium Fluoride → HCID 11497948、化合物

HRID 1994558ノート

反応式

HRID 1994558 の反応式
[F:1][C:2]([F:46])([F:45])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[S:31][CH:32]=[C:33]([CH2:35][O:36][Si](C(C)(C)C)(C)C)[N:34]=3)[C@H:14]2[CH3:44])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:46][C:2]([F:1])([F:45])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[S:31][CH:32]=[C:33]([CH2:35][OH:36])[N:34]=3)[C@H:14]2[CH3:44])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 86603422HCID 86603422、化合物

生成物 1

HCID 11497948HCID 11497948、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a 0° C. solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-thiazol-2-yl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (Example 178) (54.0 mg, 0.0774 mmol) in THF (10 mL) was added TBAF (194 μL of a 1M solution in THF, 0.194 mmol). The reaction was stirred at 0° C. for 30 minutes and then quenched by pouring into saturated NH4Cl (15 mL). The mixture was extracted with EtOAc (60 mL) and the organic layer was washed with water and brine (15 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (60% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-[4-(hydroxymethyl)-1,3-thiazol-2-yl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.11 (40% EtOAc/hexanes). LCMS=585.1 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.85 (s, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.70-7.73 (m, 4H), 7.36 (s, 1H), 5.52 (d, J=8.0 Hz, 1H), 5.39 (d, J=15.3 Hz, 1H), 4.81 (s, 2H), 4.55 (d, J=15.3 Hz, 1H), 3.87 (m, 1H), 0.69 (d, J=6.7 Hz, 3H).

後処理

  1. customquenched
  2. additionby pouring into saturated NH4Cl (15 mL)
  3. extractionThe mixture was extracted with EtOAc (60 mL)
  4. washthe organic layer was washed with water and brine (15 mL each)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by flash chromatography on silica gel (60% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-cc57f3c8280a44b5b496f7bf729d7942
出典データセット
uspto-grants-2010_01
特許番号
US07652049B2

反応ノート

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