Ethyl bromopyruvate → Ethyl 2-(3-hydroxy-4-methylphenylamino)oxazole-4-carboxylate

HRID 1474008

Reaction equation

HRID 1474008 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].Br[CH2:14][C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C.CCOC(C)=O>[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[O:11][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 85554(3-Hydroxy-p-tolyl)urea

Product 1

HCID 68491443Ethyl 2-(3-hydroxy-4-methylphenylamino)oxazole-4-carboxylateYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution containing 1-(3-hydroxy-4-methylphenyl)urea (150 mg, 0.9 mmol) and ethyl 3-bromopyruvate (0.11 mL, 0.9 mmol) in dry DMF (3.611E) was heated at 60° C. for 6 h. The reaction mixture was diluted with EtOAc and washed with brine and saturated NaHCO3 solution and the combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography on silica gel (hexane:EtOAc 6/4) to give the product in 50% yield (119 mg).

Workup

  1. washwashed with brine and saturated NaHCO3 solution
  2. dry with materialthe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography on silica gel (hexane:EtOAc 6/4)
  5. customto give the product in 50% yield (119 mg)

Sources & evidence

ORD record
ord-5190e91344024ebea7a6c9abb9757fb5
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Linked notes

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