Trifluoroacetic acid → 2-methyl-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzoic acid

HRID 1770642ノート

反応式

HRID 1770642 の反応式
[CH3:1][C:2]1[CH:14]=[C:13]([C:15]2[CH2:19][C@:18]([C:24]3[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6]C(C)(C)C)=[O:5].FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:14]=[C:13]([C:15]2[CH2:19][C@:18]([C:24]3[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([OH:6])=[O:5]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86727016tert-butyl 2-methyl-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzoate

生成物 1

HCID 867270182-methyl-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzoic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl 2-methyl-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzoate (64.87 mmol, 33 g) in dichloromethane (300 mL) was added trifluoroacetic acid (389.2 mmol, 44.6 g) at 0° C. After addition the reaction was brought to room temperature and the mixture stirred over night after which time LC-MS analysis showed a complete conversion. The crude mixture was concentrated and the residue dissolved in 300 mL of ethylacetate, washed with brine, dried over MgSO4 and evaporated to yield crude title product which was purified over a silica gel column (eluent: CH2Cl2/EtOAc) to obtain the desired product as pale yellow foam. LCMS (Method GR) RT 1.23 min, [M+H]+ 450/452; 1H-NMR (CDCl3, 400 MHz): 2.7 (s, 3H), 3.70 (d, 2H), 4.10 (d, 2H), 7.60 (s, 3H), 7.01 (d, 1H), 8.15 (d, 2H), 7.01 (d, 1H), 8.15 (d, 2H), 11.40 (s, 1H); 19F-NMR (CDCl3, 376 MHz): −79.38.

後処理

  1. additionAfter addition the reaction
  2. customwas brought to room temperature
  3. concentrationThe crude mixture was concentrated
  4. dissolutionthe residue dissolved in 300 mL of ethylacetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto yield crude title product which
  9. customwas purified over a silica gel column (eluent: CH2Cl2/EtOAc)

出典と根拠

ORDレコード
ord-2f76df525dff49ffa877ecb6f8d99fad
出典データセット
uspto-grants-2016_02
特許番号
US09247740B2

反応ノート

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