Hydrogen Bromide → (S)-tert-Butyl (4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-yl)carbamate

HRID 81291

반응식

HRID 81291 반응식
[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[C:9](=[O:13])[CH:10]=[N+]=[N-])([CH3:4])([CH3:3])[CH3:2].[BrH:25]>C1COCC1>[Br:25][CH2:10][C:9](=[O:13])[C@@H:8]([NH:7][C:6](=[O:24])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1

참가 물질

4

반응물 2

HCID 260Hydrogen BromideHCID 86617183(S)-[3-diazo-1-(4-nitrobenzyl)-2-oxo-propyl]-carbamic acid tert-butyl ester

생성물 1

HCID 53778469(S)-tert-Butyl (4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-yl)carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a 0° C. solution of (S)-[3-diazo-1-(4-nitrobenzyl)-2-oxo-propyl]-carbamic acid tert-butyl ester, 6, (0.350 g, 1.04 mmol) in THF (5 mL) is added dropwise 48% aq. HBr (0.14 mL, 1.25 mmol). The reaction mixture is stirred at 0° C. for 1.5 hours then the reaction is quenched at 0° C. with sat. Na2CO3. The mixture is extracted with EtOAc (3×25 mL) and the combined organic extracts are washed with brine, dried (Na2SO4), filtered and concentrated to obtain 0.400 g of the product which is used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 8.20 (d, J=8.4 Hz, 2H), 7.39 (d, J=8.4 Hz, 2H), 5.06 (d, J=7.8 Hz, 1H), 4.80 (q, J=6.3 Hz, 1H), 4.04 (s, 2H), 1.42 (s, 9H).

후처리

  1. customthe reaction is quenched at 0° C. with sat. Na2CO3
  2. extractionThe mixture is extracted with EtOAc (3×25 mL)
  3. washthe combined organic extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c189d82051974adb935afc8e461f1677
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846685B2

연결된 노트

불러오는 중…