Ethyl bromopyruvate → Ethyl oxazole-4-carboxylate

HRID 70841Notes

Reaction equation

HRID 70841 reaction equation
C(OC(=O)C[C@H]([NH:20][C:21](N)=[O:22])CC1C=CC(C2C=CC=CC=2)=CC=1)C.Br[CH2:26][C:27](=O)[C:28]([O:30][CH2:31][CH3:32])=[O:29]>CCO>[CH2:31]([O:30][C:28]([C:27]1[N:20]=[CH:21][O:22][CH:26]=1)=[O:29])[CH3:32]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 59607699HCID 59607699, compound

Product 1

HCID 2763217Ethyl oxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of (R)-4-biphenyl-4-yl-3-ureido-butyric acid ethyl ester (169 mg, 0.518 mmol) in EtOH (5 ml) at ice bath is added ethyl bromopyruvate (0.098 ml, 0.777 mmol). The reaction is warmed up slowly to room temperature and stirred at reflux overnight. The reaction is concentrated and the residue is taken up in EtOAc and H2O. The combined organic layer is washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2-(R)-1-biphenyl-4-ylmethyl-2-ethoxycarbonyl-ethylamino)-oxazole-4-carboxylic acid ethyl ester. HPLC retention time=1.42 minutes (condition B); MS (m+1)=423.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction is concentrated
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dbce352a00364816a63b1e7008a8ba72
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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