Potassium Fluoride → (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-fluoro-6-methylpyrimidin-4-yl)oxazolidin-2-one

HRID 57355노트

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HRID 57355 반응식
[F-:1].[K+].[C:3]([O:7][C@@H:8]([C@H:10]1[CH2:14][O:13][C:12](=[O:15])[N:11]1[C:16]1[CH:21]=[C:20]([CH3:22])[N:19]=[C:18](Cl)[N:17]=1)[CH3:9])([CH3:6])([CH3:5])[CH3:4]>CS(C)=O.C(OCC)(=O)C.O>[C:3]([O:7][C@@H:8]([C@H:10]1[CH2:14][O:13][C:12](=[O:15])[N:11]1[C:16]1[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([F:1])[N:17]=1)[CH3:9])([CH3:6])([CH3:5])[CH3:4]

참가 물질

6

반응물 2

HCID 522689Potassium FluorideHCID 90414673(R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-chloro-6-methylpyrimidin-4-yl)oxazolidin-2-one

생성물 1

HCID 90414686(R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-fluoro-6-methylpyrimidin-4-yl)oxazolidin-2-one

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

Potassium fluoride (0.063 g, 1.08 mmol, 10 equiv) was added to a solution of (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-chloro-6-methylpyrimidin-4-yl)oxazolidin-2-one (34 mg, 0.108 mmol) in DMSO (1.1 mL). The suspension was heated at 120° C. for 3 hours and then cooled to room temperature. The reaction was diluted with ethyl acetate (20 mL) and water (20 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to give crude (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-fluoro-6-methylpyrimidin-4-yl)oxazolidin-2-one, which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.99 (d, J=3.8 Hz, 1H), 4.71 (m, 1H), 4.65 (m, 1H), 4.46 (m, 1H), 4.41 (m, 1H), 2.53 (s, 3H), 1.25 (s, 9H), 1.03 (d, J=6.5 Hz, 3H); MS m/z 298.2 (M+H)+; Rt-0.96 min.

후처리

  1. temperaturecooled to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (20 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d407e169777347ecab5b4db92a94ab1a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

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