Acetic Anhydride → rac-Linezolid

HRID 1472497

反応式

HRID 1472497 の反応式
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][CH:31]([CH2:33][NH2:34])[O:30][C:29]2=[O:35])[CH:19]=[CH:20][C:21]=1[N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(N(CC)CC)C.[C:43](OC(=O)C)(=[O:45])[CH3:44]>ClCCl>[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][CH:31]([CH2:33][NH:34][C:43](=[O:45])[CH3:44])[O:30][C:29]2=[O:35])[CH:19]=[CH:20][C:21]=1[N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1

参加物

6

反応物 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 227145793-Fluoro-4-morpholinylphenyl-5-aminomethyl-1,3-oxazolidin-2-one

生成物 1

HCID 3929rac-Linezolid収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a reaction flask were added 6.53 mmol of dihydrochloride of 3-(3-fluoro-4-morpholinylphenyl-5-aminomethyl-1,3-oxazolidin-2-one (5a), 100 ml of dichloromethane and 2.95 ml (21.2 mmol) of triethylamine. Then 0.8 ml (8.45 mmol) of acetic anhydride was added while being stirred in an ice-bath. The mixture was then allowed to react at room temperature for 2 hours before being washed successively with 5% aqueous NaOH solution and saturated aqueous NaCl solution. The organic layer was then dried by anhydrous sodium sulfate and filtered, and subsequently put under reduced pressure for solvent removal. The residue was then subjected to recrystallization using ethyl acetate to give white needle crystals at a yield of 85%, HR-TOF-MS (+Q) m/z: 338.1520 (Calculated [C16H20FN3O4+H]+: 338.1516).

後処理

  1. customto react at room temperature for 2 hours
  2. washbefore being washed successively with 5% aqueous NaOH solution and saturated aqueous NaCl solution
  3. dry with materialThe organic layer was then dried by anhydrous sodium sulfate
  4. filtrationfiltered
  5. customsubsequently put under reduced pressure for solvent removal
  6. customThe residue was then subjected to recrystallization
  7. customto give white needle crystals at a yield of 85%, HR-TOF-MS (+Q) m/z

出典と根拠

ORDレコード
ord-105550dc7a56445f8ca6182f96d8c40a
出典データセット
uspto-grants-2015_04
特許番号
US09012631B2

関連ノート

読み込み中…