Acetic Acid → 4-Carboxymethyl-3-formyl-1,3-oxazolidin-5-one
Reaction equation
[CH:1]([NH:3][C@@H:4]1[C:9](=[O:10])[O:8][C:6](=O)C1)=[O:2].C=O.[C:13]([OH:16])(=[O:15])[CH3:14]>>[C:13]([CH2:14][CH:4]1[C:9](=[O:10])[O:8][CH2:6][N:3]1[CH:1]=[O:2])([OH:16])=[O:15]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
14.3 g (100 mmol) of formyl aspartic acid anhydride are charged into a 100° C. solution of 9 g (300 mmol) paraformaldehyde in 200 ml glacial acetic acid. After 30 min the mixture is cooled to 50° C. and the acetic acid removed in a vacuum. Then, the yellowish oily residue is taken up in a little saturated sodium hydrogen carbonate solution and extracted several times after acidification of the aqueous solution to pH 1.5 with ethyl acetate. The collected organic phases are dried over magnesium sulfate and then filtered. After removal of the solvent in a vacuum a yellowish oil is obtained.
Workup
- customthe acetic acid removed in a vacuum
- extractionextracted several times after acidification of the aqueous solution to pH 1.5 with ethyl acetate
- dry with materialThe collected organic phases are dried over magnesium sulfate
- filtrationfiltered
- customAfter removal of the solvent in a vacuum a yellowish oil
- customis obtained
Sources & evidence
- ORD record
- ord-f48ec3860ce04799b5a1c007828d3cc6
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06437145B1
Reaction notes
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