Acetic Anhydride → Linezolid

HRID 245320

반응식

HRID 245320 반응식
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:11]([F:21])[CH:10]=2)[CH2:4]1.[C:22](OC(=O)C)(=[O:24])[CH3:23].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:23][C:22]([NH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[C:11]([F:21])[CH:10]=2)[CH2:4]1)=[O:24]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10780199(5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinone

생성물 1

HCID 441401Linezolid수율 88.9%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

(S)-5-(aminomethyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one (0.3 g, 1 mmol), acetic anhydride (0.12 g, 1.2 mmol) and triethylamine (0.5 g, 5 mmol) were added to 10 mL ethyl acetate and the reaction mixture was stirred at room temperature for 2 hours. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, most part of the solvent was evaporated, frozen crystallized and filtered to yield the crude product. The crude product was recrystallized with ethyl acetate to provide 0.30 g of linezolid in 88% yield.

후처리

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. custommost part of the solvent was evaporated
  5. temperaturefrozen
  6. customcrystallized
  7. filtrationfiltered
  8. customto yield the crude product
  9. customThe crude product was recrystallized with ethyl acetate

출처 및 근거

ORD 기록
ord-28569bd637f947beb183784d41d0f04b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658789B2

연결된 노트

불러오는 중…