Ethyl bromopyruvate → HCID 59607552, compound

HRID 1945018Notes

Reaction equation

HRID 1945018 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@H:6]([NH:20][C:21]([NH2:23])=[O:22])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH3:2].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:23]=[C:21]([NH:20][C@H:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:24])[O:22][CH:26]=1)=[O:29])[CH3:32]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 59607699HCID 59607699, compound

Product 1

HCID 59607552HCID 59607552, compound

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-b787f4b0a335440ba71f39df1e966b63
Source dataset
uspto-grants-2013_03
Patent number
US08394853B2

Reaction notes

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