Sodium hydride → (5S)-3-(4-(3,6-Dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-(2-oxo-1H-pyridin-1-ylmethyl)oxazolidin-2-one

HRID 723794노트

반응식

HRID 723794 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[O:10]1[CH2:15][CH:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][C@H:25]([CH2:27]OS(C)(=O)=O)[O:24][C:23]3=[O:33])=[CH:18][C:17]=2[F:34])[CH2:12][CH2:11]1>CN(C)C=O>[O:10]1[CH2:11][CH:12]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][C@H:25]([CH2:27][N:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]4=[O:1])[O:24][C:23]3=[O:33])=[CH:18][C:17]=2[F:34])[CH2:14][CH2:15]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 213566765(R)-methanesulfonyloxymethyl 3-(4-[3,6-dihydro-(2H)-pyran-4-yl]-3-fluorophenyl)oxazolidin-2-oneHCID 178516071HCID 178516071, 화합물

생성물 1

HCID 44354874(5S)-3-(4-(3,6-Dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-(2-oxo-1H-pyridin-1-ylmethyl)oxazolidin-2-one수율 28.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-Hydroxypyridine (108 mg, 1.14 mM) was added at room temperature, under an atmosphere of nitrogen, to a stirred suspension of sodium hydride (60% dispersion in oil, 48 mg, 1.2 mM) in N,N-dimethylformamide (5 ml). The reaction was stirred for 30 minutes then (5R)-3-(4-(3,6-dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-methanesulfonyloxymethyloxazolidin-2-one (400 mg, 1.08 mM; WO 97-09328) was added in one portion. The mixture was stirred and heated at 60° for 5 hour before quenching in water (20 ml) and extracting with ethyl acetate. The extract was washed twice with water and once with saturated brine, dried (magnesium sulfate) and evaporated to an orange oil, which was purified by flash chromatography on silica, eluting with 2.5% methanol in dichloromethane to give the title compound (115 mg) as a colourless solid.

후처리

  1. stirringThe mixture was stirred
  2. temperatureheated at 60° for 5 hour
  3. custombefore quenching in water (20 ml)
  4. extractionextracting with ethyl acetate
  5. washThe extract was washed twice with water and once with saturated brine
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated to an orange oil, which
  8. customwas purified by flash chromatography on silica
  9. washeluting with 2.5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-4cca95dca340460f912052089e70f7ef
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141583B2

반응 노트

불러오는 중…