Acetic Anhydride → rac-Linezolid

HRID 1472497

반응식

HRID 1472497 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 3929rac-Linezolid수율 85%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-105550dc7a56445f8ca6182f96d8c40a
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012631B2

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