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

HRID 83517Notes

Reaction equation

HRID 83517 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6386tert-ButanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-050e667941c042f1a9a63cc20ed78f75
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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