Benzyl chloroformate → (R)-benzyl 3-methyl-3-((R)-2-oxo-4-phenyloxazolidine-3-carbonyl)pyrrolidine-1-carboxylate

HRID 338826

반응식

HRID 338826 반응식
C([N:8]1[CH2:12][CH2:11][C@:10]([CH3:27])([C:13]([N:15]2[C@H:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][O:17][C:16]2=[O:26])=[O:14])[CH2:9]1)C1C=CC=CC=1.C([O-])(O)=O.[Na+].[CH2:33]([O:40][C:41](Cl)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>ClCCCl.Cl>[CH3:27][C@@:10]1([C:13]([N:15]2[C@H:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][O:17][C:16]2=[O:26])=[O:14])[CH2:11][CH2:12][N:8]([C:41]([O:40][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:42])[CH2:9]1

참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 70983198(R)-3-((S)-1-benzyl-3-methylpyrrolidine-3-carbonyl)-4-phenyloxazolidin-2-one

생성물 1

HCID 86707397(R)-benzyl 3-methyl-3-((R)-2-oxo-4-phenyloxazolidine-3-carbonyl)pyrrolidine-1-carboxylate수율 52.2%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매2회HCID 313Hydrochloric Acid용매

실험 절차

To a suspension of (R)-3-((S)-1-benzyl-3-methylpyrrolidine-3-carbonyl)-4-phenyloxazolidin-2-one (145.50 g, 399.25 mmol) and NaHCO3 (33.54 g, 399.25 mmol) in dry DCE (1000 mL) at ambient temperature was added dropwise a solution of benzylchloroformate (134.87 mL, 958.19 mmol) in DCE (100 mL) and the reaction was stirred at ambient temperature for 24 hours. The reaction was diluted with 1N HCl (500 mL) and the layers were separated. The organic layer was washed with 1M HCl (250 mL), dried (MgSO4), filtered and concentrated under reduced pressure to a thick yellow residue. The residue was purified by flash chromatography (5% ethyl acetate/DCM) to give (R)-benzyl 3-methyl-3-((R)-2-oxo-4-phenyloxazolidine-3-carbonyl)pyrrolidine-1-carboxylate (85.1 g, 208.35 mmol, 52.2% yield).

후처리

  1. customthe layers were separated
  2. washThe organic layer was washed with 1M HCl (250 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a thick yellow residue
  6. customThe residue was purified by flash chromatography (5% ethyl acetate/DCM)

출처 및 근거

ORD 기록
ord-b5e7317898804ea0a861439111aac533
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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