Hydrochloric Acid → 2-Hydroxy-1,3-oxazole-5-carboxylic acid

HRID 1480424Notes

Reaction equation

HRID 1480424 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9]CC)=[O:8])[O:3]1.O[Li].O.Cl.O1CCOCC1>C1COCC1.O.CO>[O:1]=[C:2]1[NH:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[O:3]1

Participants

8

Procedure

To a solution of ethyl 2-oxo-2,3-dihydrooxazole-5-carboxylate (300 mg, 1.909 mmol) in THF (5 ml) was added LiOH.H2O (352 mg, 8.4 mmol) as a solution in water (5 ml). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. To the residue was added 4M HCl in dioxane (6 ml, 24.0 mmol) and the solid was sonicated for ˜1 minute. The solvent was removed under reduced pressure to afford a yellow solid. The solid was redissolved in MeOH and concentrated under reduced pressure. The solid was dried in the vacuum oven to afford the title compound;

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe solid was sonicated for ˜1 minute
  3. customThe solvent was removed under reduced pressure
  4. customto afford a yellow solid
  5. concentrationconcentrated under reduced pressure
  6. customThe solid was dried in the vacuum oven

Sources & evidence

ORD record
ord-ce4dc1460c774925a7a1d2c358c6466f
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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