2-AMINO-OXAZOLE-5-CARBOXYLIC ACID ETHYL ESTER Chemical Properties

Melting point:

151-153

Boiling point:

282.9±32.0 °C(Predicted)

Density 

1.278±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

pka

3.39±0.10(Predicted)

color 

Off white

InChI

InChI=1S/C6H8N2O3/c1-2-10-5(9)4-3-8-6(7)11-4/h3H,2H2,1H3,(H2,7,8)

InChIKey

UHUDJKCNXFBBHU-UHFFFAOYSA-N

SMILES

O1C(C(OCC)=O)=CN=C1N

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2934999090

2-AMINO-OXAZOLE-5-CARBOXYLIC ACID ETHYL ESTER Usage And Synthesis

Synthesis

GENERAL STEPS: Ethyl 2-chloro-3-oxopropionate (13) (4.48 g, 29.8 mmol, 1.00 equiv) and urea (1.79 g, 29.8 mmol, 1.00 equiv) were dissolved in 40 mL of water. The reaction mixture was stirred at 100 °C for 1 hour. After completion of the reaction, the light yellow suspension was cooled to room temperature and neutralized with saturated NaHCO3 solution. Subsequently, the reaction mixture was extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by fast liquid chromatography (silica gel, n-hexane/ethyl acetate = 1/2) to afford ethyl 2-aminooxazole-5-carboxylate (14) (2.40 g, 15.4 mmol, 51.3% yield).

References

[1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 754 - 761

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