Tetrahydrofuran → (S)-4-Benzyl-3-(4-methylpentanoyl)oxazolidin-2-one

HRID 341369노트

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HRID 341369 반응식
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.C([Li])CCC.[CH3:24][CH:25]([CH3:31])[CH2:26][CH2:27][C:28](Cl)=[O:29].C([O-])(O)=O.[Na+]>CCCCCC>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:28](=[O:29])[CH2:27][CH2:26][CH:25]([CH3:31])[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 5

HCID 8028TetrahydrofuranHCID 170008Pentanoyl chloride, 4-methyl-HCID 516892Sodium BicarbonateHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

생성물 1

HCID 10869526(S)-4-Benzyl-3-(4-methylpentanoyl)oxazolidin-2-one수율 62%

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
-78 °C

실험 절차

(S)-4-Benzyl-2-oxazolidinone (15.1 g, 85.0 mmol) was dissolved in THF (200 mL, 2.5 mol), cooled at −78° C. under nitrogen, and stirred for 10 minutes. 1.6 M of n-butyllithium in hexane (53.1 mL) was added dropwise and stirred for 15 minutes. 4-Methylpentanoyl chloride (12.6 g, 93.5 mmol) was added dropwise, stirred for 30 minutes at −78° C., then warmed to 0° C. for 2 hours. 150 mL of saturated NaHCO3 was added and the mixture was warmed to room temperature for 30 minutes. The mixture was extracted with DCM, washed with Na2CO3 (5%) and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. Excess oxazolidinone was removed using hexanes to provide intermediate (2a) (14.5 g).

후처리

  1. stirringstirred for 15 minutes
  2. stirringstirred for 30 minutes at −78° C.
  3. temperaturewarmed to 0° C. for 2 hours
  4. temperaturethe mixture was warmed to room temperature for 30 minutes
  5. extractionThe mixture was extracted with DCM
  6. washwashed with Na2CO3 (5%) and saturated aqueous NaCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customExcess oxazolidinone was removed

출처 및 근거

ORD 기록
ord-945ae85614bb4ab19db6ac2c19d154aa
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895755B2

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