Ethyl Acetate → HCID 58005143, 화합물

HRID 389189노트

반응식

HRID 389189 반응식
BrC1C=CC(S([O:11][C@@H:12]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)(=O)=O)=CC=1.[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[NH:35][C:34]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[CH:33][C:32]2=O.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CN1CCCC1.O>[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[C:34]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH:33]=[C:32]2[O:11][C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 57617105HCID 57617105, 화합물

생성물 1

HCID 58005143HCID 58005143, 화합물수율 92.1%

시약·촉매·용매 2

HCID 962Water용매HCID 84541-Methylpyrrolidine용매

반응 조건

온도
45 °C

실험 절차

To a solution of the product from Step 4 (19.4 g, 41.7 mmol) and 6-bromo-7-methoxy-2-phenylquinolin-4(1H)-one (Step 3, 13.5 g, 40.9 mmol) in N-methylpyrrolidine (200 mL) was added cesium carbonate (20.0 g, 61.3 mmol). The reaction mixture was then heated at 45° C. with stirring for 15 hours and cooled to RT. The reaction mixture was poured into EtOAc and water, and the white solids removed by filtration. The layers were separated, and the organic phase washed with saturated aqueous NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica (gradient elution 10% to 50% EtOAc in hexanes) to give the title compound (21.0 g) as a pale yellow solid. LRMS (M+H)+ Calcd.: 557.1; found 557.3.

후처리

  1. temperaturecooled to RT
  2. customthe white solids removed by filtration
  3. customThe layers were separated
  4. washthe organic phase washed with saturated aqueous NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica (gradient elution 10% to 50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-0f175e9a63e44596add6b0d783865b9b
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377874B2

반응 노트

불러오는 중…