Tetrahydrofuran → 2-Aminooxazole-5-carboxylic acid

HRID 2234428Notes

Reaction equation

HRID 2234428 reaction equation
C(OC([C:6]1[N:7]=[C:8]([NH2:11])[O:9][CH:10]=1)=O)C.[OH2:12].[OH-].[Li+].C1[CH2:19][O:18]CC1>O>[NH2:11][C:8]1[O:9][C:10]([C:19]([OH:18])=[O:12])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 319549Ethyl 2-amino-1,3-oxazole-4-carboxylate

Product 1

HCID 467390742-Aminooxazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl2-aminooxazole-4-carboxylate (Apollo Scientific; 1.175 g, 7.50 mmol) was dissolved in THF (15 mL) and water (8 mL). Lithium hydroxide monohydrate (1.58 g, 37.52 mmol) was added and the mixture stirred overnight at room temperature. The mixture was neutralised with 2N HCl(aqu) and concentrated. The residue was suspended in water and filtered and the solid collected dissolved in 2N NaOH(aqu), filtered and then acidified with acetic acid to approximately pH4. The mixture was allowed to stand in an ice bath for 10 minutes and then filtered. The solid was dried on the filter and then in a dessicator overnight to give the title compound a s a yellow solid (194 mg, 20%)

Workup

  1. concentrationconcentrated
  2. filtrationfiltered
  3. customthe solid collected
  4. dissolutiondissolved in 2N NaOH(aqu)
  5. filtrationfiltered
  6. waitto stand in an ice bath for 10 minutes
  7. filtrationfiltered
  8. customThe solid was dried on the
  9. filtrationfilter

Sources & evidence

ORD record
ord-1be3781ed888494596952880f38cdd62
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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