Citric Acid → (R)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid

HRID 1724720Notes

Reaction equation

HRID 1724720 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([O:15]C)=[O:14])[CH2:11][O:10][C:9]1([CH3:18])[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([OH:15])=[O:14])[CH2:11][O:10][C:9]1([CH3:18])[CH3:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 6882203-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate

Product 1

HCID 6932185(R)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acidYield 47.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. additionis added
  2. concentrationTHF is concentrated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. customThe organic phase is dried on MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-93aca3c42f1340daaa14c8fbb1bca918
Source dataset
uspto-grants-2009_02
Patent number
US07488755B2

Reaction notes

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