Sodium hydride → (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2,6-dichloropyrimidin-4-yl)oxazolidin-2-one

HRID 57342

반응식

HRID 57342 반응식
[H-].[Na+].[Cl:3][C:4]1[N:9]=[C:8](Cl)[CH:7]=[C:6]([Cl:11])[N:5]=1.[C:12]([O:16][C@@H:17]([C@H:19]1[CH2:23][O:22][C:21](=[O:24])[NH:20]1)[CH3:18])([CH3:15])([CH3:14])[CH3:13].CCOC(C)=O.CCCCCCC>CN(C=O)C.CCOC(C)=O>[C:12]([O:16][C@@H:17]([C@H:19]1[CH2:23][O:22][C:21](=[O:24])[N:20]1[C:8]1[CH:7]=[C:6]([Cl:11])[N:5]=[C:4]([Cl:3])[N:9]=1)[CH3:18])([CH3:13])([CH3:14])[CH3:15]

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 773782,4,6-TrichloropyrimidineHCID 21899848Ethylacetate heptaneHCID 90414930(R)-4-((R)-1-(tert-butoxy)ethyl)oxazolidin-2-one

생성물 1

HCID 90414426(R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2,6-dichloropyrimidin-4-yl)oxazolidin-2-one수율 65.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a round bottom flask was added NaH (0.54 g, 13.5 mmol, 57% dispersion in mineral oil) to a solution of 2,4,6-trichloropyrimidine (1.22 ml, 10.6 mmol) and (R)-4-((R)-1-(tert-butoxy)ethyl)oxazolidin-2-one (1.8 g, 9.61 mmol) in DMF (32 mL) at 0° C. (ice bath) under a bubbler. The yellow suspension was then stirred at 0° C. for 15 min and then the ice bath was removed and reaction mixture allowed to stir 1 hr at room temperature. Reaction mixture was diluted with EtOAc and then carefully quenched with brine. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated onto silica gel. Silica gel column chromatography (EtOAc/Heptane 0 to 100%) provided (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2,6-dichloropyrimidin-4-yl)oxazolidin-2-one (2.1 g, 6.28 mmol, 65% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.04 (d, J=6.55 Hz, 3H) 1.26 (s, 9H) 4.38-4.48 (m, 2H) 4.64-4.75 (m, 2H) 8.22 (s, 1H). LCMS m/z 334.1 (M+H)+, Rt 1.10 min.

후처리

  1. customthe ice bath was removed
  2. customreaction mixture
  3. stirringto stir 1 hr at room temperature
  4. customReaction mixture
  5. customcarefully quenched with brine
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with EtOAc
  8. dry with materialThe combined organic layers were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated onto silica gel

출처 및 근거

ORD 기록
ord-a7e31ec28616490589153cf7ac4b0516
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

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