Dimethylformamide → (S)-2-[3-(2,4-dichlorobenzyl)-8-fluoro-4-methyl-2-oxo-1,2-dihydroquinolin-5-yloxy]propionic Acid Methyl Ester

HRID 2266611

반응식

HRID 2266611 반응식
[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][C:5]1[C:6](=[O:18])[NH:7][C:8]2[C:13]([C:14]=1[CH3:15])=[C:12]([OH:16])[CH:11]=[CH:10][C:9]=2[F:17].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:35][O:36][C:37](=[O:41])[C@H:38](Cl)[CH3:39]>O>[CH3:35][O:36][C:37](=[O:41])[C@@H:38]([O:16][C:12]1[CH:11]=[CH:10][C:9]([F:17])=[C:8]2[C:13]=1[C:14]([CH3:15])=[C:5]([CH2:4][C:3]1[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:2]=1[Cl:1])[C:6](=[O:18])[NH:7]2)[CH3:39]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 149593Methyl 2-chloropropanoate, (R)-HCID 68785818HCID 68785818, 화합물

생성물 1

HCID 68780492(S)-2-[3-(2,4-dichlorobenzyl)-8-fluoro-4-methyl-2-oxo-1,2-dihydroquinolin-5-yloxy]propionic Acid Methyl Ester

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

A mixture of 3-(2,4-dichlorobenzyl)-8-fluoro-5-hydroxy-4-methyl-1H-quinolin-2-one (0.40 g), N,N-dimethylformamide (5.0 mL), potassium carbonate (0.17 g) and (R)-2-chloropropionic acid methyl ester (0.15 g) was stirred at 40° C. for 24 hours. The mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed saturated aqueous sodium chloride solution, dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of toluene, dichloromethane and ethyl acetate (1:1:0 to 0:1:0 to 0:10:1 by volume) to afford title compound as a cream solid, 0.21 g.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with a mixture of toluene, dichloromethane and ethyl acetate (1:1:0 to 0:1:0 to 0:10:1 by volume)

출처 및 근거

ORD 기록
ord-d46cc373424942e29507fdbb2011fa86
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858640B2

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