Trifluoroacetic acid → (1S)-1-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethan-1-amine

HRID 57396ノート

反応式

HRID 57396 の反応式
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]=[C:18]([C@@H:20]([NH:22]C(=O)OC(C)(C)C)[CH3:21])[O:17][N:16]=2)=[CH:11][CH:10]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]=[C:18]([C@@H:20]([NH2:22])[CH3:21])[O:17][N:16]=2)=[CH:13][CH:14]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 90414461(S)-tert-butyl 1-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethylcarbamate

生成物 1

HCID 40800146(1S)-1-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethan-1-amine収率 118.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2,2,2-Trifluoroacetic acid (4 mL, 52 mmol) was added to a solution of (S)-tert-butyl 1-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethylcarbamate (0.613 g, 1.89 mmol) in DCM (10 mL) at room temperature. The solution was stirred at room temperature for 1 hour and then concentrated in vacuo. The residue was dissolved in chloroform (100 mL) and washed with saturated aqueous sodium bicarbonate (100 mL). The layers were separated and the aqueous layer was extracted with chloroform (3×30 mL) and the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give (S)-1-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethanamine (500 mg, yellow oil). The material was used without further purification. 1H NMR (400 MHz, CDCl3) δ 8.04 (d, J=8.7 Hz, 2H), 7.47 (d, J=8.6 Hz, 2H), 4.37 (q, J=6.9 Hz, 1H), 1.62 (d, J=6.9 Hz, 3H). MS m/z 224.0 (M+H)+; Rt-0.56 min.

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in chloroform (100 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (100 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with chloroform (3×30 mL)
  6. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-063b41892a8441e592a5536359e05a67
出典データセット
uspto-grants-2016_09
特許番号
US09434719B2

反応ノート

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