Hydrochloric Acid → 2-Hydroxy-1,3-oxazole-5-carboxylic acid
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]1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
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
- customThe solvent was removed under reduced pressure
- customthe solid was sonicated for ˜1 minute
- customThe solvent was removed under reduced pressure
- customto afford a yellow solid
- concentrationconcentrated under reduced pressure
- 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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