HuagongsheHuagongshe Chemistry Print Report · For research reference only
Citric Acid → (R)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | 3-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate | HCID 688220 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (R)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid | HCID 6932185 | 47.9% |
Reaction Steps
Methyl 3-tert-butoxycarbonyl-2,2-dimethyloxazolidine-4-(R)-carboxylate (3.0 g) is dissolved in a mixture of tetrahydrofurane (THF)/H2O (3/1; 30 ml), and LiOH.H2O (684 mg) is added. After being subjected to agitation for 3 hours at room temperature, the reaction mixture is acidified with citric acid 1N (11 ml). THF is concentrated and the aqueous phase is extracted with ethyl acetate. The organic phase is dried on MgSO4, filtered and concentrated to obtain the expected product as a viscous orange oil (1.36 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07488755B2 |
| Source dataset | uspto-grants-2009_02 |
| ORD ID | ord-93aca3c42f1340daaa14c8fbb1bca918 |
| Source note | uspto-grants-2009_02 |