Acetic Anhydride → Linezolid

HRID 245320

反応式

HRID 245320 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 441401Linezolid収率 88.9%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-28569bd637f947beb183784d41d0f04b
出典データセット
uspto-grants-2014_02
特許番号
US08658789B2

関連ノート

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