Triethylamine → HCID 76849200、化合物

HRID 921716ノート

反応式

HRID 921716 の反応式
[C:1]([C:4]1[N:9]=[C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:6][CH:5]=1)(=O)[NH2:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C:1]([C:4]1[N:9]=[C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH:7]=[CH:6][CH:5]=1)#[N:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 86708592HCID 86708592、化合物

生成物 1

HCID 76849200HCID 76849200、化合物収率 62%

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 round bottom flask charged with tert-butyl (6-carbamoylpyridin-2-yl)carbamate (0.940 g, 3.96 mmol) in dichloromethane (7.92 ml) was added triethylamine (1.380 ml, 9.90 mmol). The reaction mixture was cooled to 0° C. and trifluoroacetic anhydride (0.671 ml, 4.75 mmol) was added dropwise. The reaction mixture was stirred at 0° C. 90 min. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and transferred to a separatory funnel. The aqueous layer was extracted with dichloromethane (2×). The combined organics were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by column chromatography on the ISCO system (40 g, 0-15% EtOAc/Hex) to provide tert-butyl (6-cyanopyridin-2-yl)carbamate (0.538 g).

後処理

  1. custom90 min
  2. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  3. customtransferred to a separatory funnel
  4. extractionThe aqueous layer was extracted with dichloromethane (2×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by column chromatography on the ISCO system (40 g, 0-15% EtOAc/Hex)

出典と根拠

ORDレコード
ord-911cc26d13824ffa9a6b88ce2e5285c4
出典データセット
uspto-grants-2016_03
特許番号
US09273057B2

反応ノート

読み込み中…