Triethylamine → HCID 76849200, 화합물

HRID 921716노트

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HRID 921716 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 86708592HCID 86708592, 화합물

생성물 1

HCID 76849200HCID 76849200, 화합물수율 62%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-911cc26d13824ffa9a6b88ce2e5285c4
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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