Pyridine → (R)-2-Oxoimidazolidine-1,5-dicarboxylic Acid 1-benzyl ester 5-tert-butyl Ester

HRID 83517노트

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HRID 83517 반응식
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([C:16]([OH:18])=[O:17])[CH2:14][NH:13][C:12]1=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1[CH:25]=[CH:24][CH:23]=CC=1.P(Cl)(Cl)(Cl)=O.[C:31]([O-])(=O)C.[Na+]>C(Cl)(Cl)Cl.C(O)(C)(C)C>[C:24]([O:17][C:16]([C@@H:15]1[N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[C:12](=[O:19])[NH:13][CH2:14]1)=[O:18])([CH3:23])([CH3:25])[CH3:31]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 688195(4R)-3-[(Benzyloxy)carbonyl]-2-oxoimidazolidine-4-carboxylic acid

생성물 1

HCID 51425954(R)-2-Oxoimidazolidine-1,5-dicarboxylic Acid 1-benzyl ester 5-tert-butyl Ester

시약·촉매·용매 2

HCID 6212Chloroform용매2회HCID 6386tert-Butanol용매

실험 절차

To a solution of (R)-2-oxoimidazolidine-1,5-dicarboxylic acid 1-benzyl ester (534 mg) in chloroform (2.6 ml) were sequentially added pyridine (1.0 ml) and tert-butylalcohol (1.5 ml) at room temperature, and the mixture was stirred. This reaction solution was iced, and phosphorous oxychloride (0.23 ml) was added thereto, and then the mixture was stirred at room temperature for 5 hours. This reaction solution was iced, and a 20 wt % aqueous solution of sodium acetate (20 ml) was added thereto, and then chloroform (5 ml) was further added at room temperature, and the mixture was stirred for 30 minutes. This mixed solution was extracted with chloroform, and the resulting organic layer was washed with a 0.1M aqueous solution of hydrochloric acid, water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude product of the titled compound (467 mg).

후처리

  1. customat room temperature
  2. stirringthe mixture was stirred at room temperature for 5 hours
  3. stirringthe mixture was stirred for 30 minutes
  4. extractionThis mixed solution was extracted with chloroform
  5. washthe resulting organic layer was washed with a 0.1M aqueous solution of hydrochloric acid, water
  6. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-050e667941c042f1a9a63cc20ed78f75
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846746B2

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