Nitrogen → Linezolid

HRID 245321

反応式

HRID 245321 の反応式
[CH2:1]([N:8]([CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[C:25]([F:35])[CH:24]=2)[CH2:18]1)CC1C=CC=CC=1)[C:2]1C=CC=CC=1.N#N.[H][H].C(OC(=O)C)(=[O:42])C.C(N(CC)CC)C>[Pd].CC(C)=O>[CH3:2][C:1]([NH:8][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[C:25]([F:35])[CH:24]=2)[CH2:18]1)=[O:42]

参加物

8

反応物 5

HCID 947NitrogenHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11213668(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 441401Linezolid収率 75.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 180Acetone溶媒

実験手順

(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one (0.95 g, 2 mmol) and 0.1 g 10 wt % Pd—C were added to 20 mL acetone and the air was replaced with N2. The reaction went on under 5 Mpa hydrogen at room temperature for 5 hours. After filtered, acetic anhydrid (0.24 g, 2.4 mmol) and triethylamine (2.0 g, 20 mmol) were added and reacted for 2 hours at room temperature. 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 provide the crude product. The crude product was recrystallized with ethyl acetate to provide 0.51 g of linezolid in 75% yield.

後処理

  1. filtrationAfter filtered
  2. customreacted for 2 hours at room temperature
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. custommost part of the solvent was evaporated
  7. temperaturefrozen
  8. customcrystallized
  9. filtrationfiltered
  10. customto provide the crude product
  11. customThe crude product was recrystallized with ethyl acetate

出典と根拠

ORDレコード
ord-7d088d57876841848e04e42cad2c39d7
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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