Hydrogen Peroxide → (S)-2-(4-bromophenyl)-2-((S)-1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidin-2-yl)acetic acid

HRID 387519노트

반응식

HRID 387519 반응식
OO.O[Li].O.C([C@@H]1COC(=O)N1[C:19](=[O:42])[C@H:20]([C@H:28]1[N:32]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:31]([CH3:41])([CH3:40])[CH2:30][CH2:29]1)[C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=1)C1C=CC=CC=1.[O-:43]S([O-])=O.[Na+].[Na+]>C1COCC1.O.C1COCC1>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([C@@H:20]([C@@H:28]2[CH2:29][CH2:30][C:31]([CH3:40])([CH3:41])[N:32]2[C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[C:19]([OH:43])=[O:42])=[CH:22][CH:23]=1

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 68735397HCID 68735397, 화합물

생성물 1

HCID 59564917(S)-2-(4-bromophenyl)-2-((S)-1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidin-2-yl)acetic acid수율 87%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

30% H2O2 (0.67 mL, 7.0 mmol) was added to a solution of LiOH—H2O (0.24 g, 5.60 mmol) in THF/water (2:1, 93 mL), and the solution was stirred at room temperature for 10 minutes. The solution was then cooled to 0° C. and treated with a solution of (S)-tert-butyl 5-((S)-2-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-(4-bromophenyl)-2-oxoethyl)-2,2-dimethylpyrrolidine-1-carboxylate (1.60 g, 2.80 mmol) in THF (10 mL). The reaction was stirred at 0° C. for 2 hours and allowed to warm to room temperature and stirred overnight. The reaction was then cooled to 0° C. and treated with 1M Na2SO3 (10 mL) and stirred for 10 minutes. The reaction was then warmed to room temperature and stirred for 10 minutes. The reaction was next concentrated and extracted with EtOAc (2×20 mL). The aqueous layer was then acidified with 1N HCl to a pH of about 1 to about 2 and extracted with DCM (2×20 mL). The combined DCM fractions were dried over sodium sulfate, filtered, and concentrated to give (S)-2-(4-bromophenyl)-2-((S)-1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidin-2-yl)acetic acid (1.01 g, 87% yield) as a solid. MS ESI (+) m/z 412 detected.

후처리

  1. temperatureThe solution was then cooled to 0° C.
  2. stirringThe reaction was stirred at 0° C. for 2 hours
  3. temperatureto warm to room temperature
  4. stirringstirred overnight
  5. temperatureThe reaction was then cooled to 0° C.
  6. stirringstirred for 10 minutes
  7. temperatureThe reaction was then warmed to room temperature
  8. stirringstirred for 10 minutes
  9. concentrationThe reaction was next concentrated
  10. extractionextracted with EtOAc (2×20 mL)
  11. extractionextracted with DCM (2×20 mL)
  12. dry with materialThe combined DCM fractions were dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1e6a07b18e6847bea1324a24aa3862d3
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372842B2

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