Hydrogen Peroxide → HCID 68734733, 화합물

HRID 387521노트

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HRID 387521 반응식
OO.O[Li].O.C([C@@H]1COC(=O)N1[C:19](=[O:43])[C@H:20]([C@H:29]1[N:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:32]([CH3:42])([CH3:41])[CH2:31][CH2:30]1)[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([F:28])[CH:22]=1)C1C=CC=CC=1.[O-:44]S([O-])=O.[Na+:48].[Na+]>C1COCC1.O>[Na+:48].[C:37]([O:36][C:34]([N:33]1[C:32]([CH3:42])([CH3:41])[CH2:31][CH2:30][C@H:29]1[C@H:20]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([F:28])[CH:22]=1)[C:19]([O-:43])=[O:44])=[O:35])([CH3:38])([CH3:39])[CH3:40]

참가 물질

7

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HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 68759221(s)-Tert-butyl 5-((s)-2-((r)-4-benzyl-2-oxooxazolidin-3-yl)-1-(4-chloro-3-fluorophenyl)-2-oxoethyl)-2,2-dimethylpyrrolidine-1-carboxylate

생성물 1

HCID 68734733HCID 68734733, 화합물수율 94%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

30% H2O2 (0.159 mL, 1.65 mmol) was added to a solution of LiOH—H2O (0.055 g, 1.32 mmol) in 2:1 THF:H2O (40 mL). The mixture was stirred for 20 minutes and then cooled to 0° C. A solution of (S)-tert-butyl 5-((S)-2-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-(4-chloro-3-fluorophenyl)-2-oxoethyl)-2,2-dimethylpyrrolidine-1-carboxylate (0.360 g, 0.660 mmol) in THF (3 mL) was next added slowly. Upon completion of the addition, the reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was then recooled to 0° C., and 1M Na2SO3 (4 mL) was added. The reaction was stirred for 10 minutes at 0° C. and then warmed to room temperature and stirred for an additional 10 minutes. The reaction was then concentrated in vacuo to remove THF, and the resulting mixture was washed with EtOAc. The organic fraction was then dried over sodium sulfate, filtered and concentrated to give (S)-2-((S)-1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidin-2-yl)-2-(4-chloro-3-fluorophenyl)acetic acid sodium salt (0.24 g, 94%) as a powder. MS ESI (+) m/z 386 detected.

후처리

  1. additionUpon completion of the addition
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. customwas then recooled to 0° C.
  5. stirringThe reaction was stirred for 10 minutes at 0° C.
  6. temperaturewarmed to room temperature
  7. stirringstirred for an additional 10 minutes
  8. concentrationThe reaction was then concentrated in vacuo
  9. customto remove THF
  10. washthe resulting mixture was washed with EtOAc
  11. dry with materialThe organic fraction was then dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7bcdde3418d547419b20a20e40e9e8bd
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372842B2

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