Lithium Hydroxide → 3-(3,3-dimethyl-2-oxopentanoyl)-1,3-oxazolidine-4-carboxylic Acid

HRID 1250188Notes

Reaction equation

HRID 1250188 reaction equation
[CH3:1][C:2]([CH3:18])([CH2:16][CH3:17])[C:3](=[O:15])[C:4]([N:6]1[CH:10]([C:11]([O:13]C)=[O:12])[CH2:9][O:8][CH2:7]1)=[O:5].[Li+].[OH-]>CO>[CH3:1][C:2]([CH3:18])([CH2:16][CH3:17])[C:3](=[O:15])[C:4]([N:6]1[CH:10]([C:11]([OH:13])=[O:12])[CH2:9][O:8][CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10956210Methyl 3-(3,3-dimethyl-2-oxopentanoyl)-1,3-oxazolidine-4-carboxylate

Product 1

HCID 101987123-(3,3-dimethyl-2-oxopentanoyl)-1,3-oxazolidine-4-carboxylic AcidYield 86.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolved methyl 3-(3,3-dimethyl-2-oxopentanoyl)-1,3-oxazolidine-4-carboxylate (3) (0.6 g, 2.33 mM) in MeOH (25 ml) and added LiOH (1M in water, 10 ml, 10 mM). Stirred this mixture overnight at room temperature. Evaporated and partitioned the residues between EtOAc (50 ml) and 2N HCl (50 mL). Extracted the aqueous layer twice more with EtOAc (2×25 ml). Combined extracts, washed with brine (50 ml), dried with anhydrous magnesium sulfate, filtered and evaporated. A clear oil product (0.49 g, 86%) was obtained. Anal. (C11H17NO5) C, H, N.

Workup

  1. customEvaporated
  2. custompartitioned the residues between EtOAc (50 ml) and 2N HCl (50 mL)
  3. extractionExtracted the aqueous layer twice more with EtOAc (2×25 ml)
  4. washCombined extracts, washed with brine (50 ml)
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-41ed44af26074d948ff707cc7aa98a9e
Source dataset
uspto-grants-2002_01
Patent number
US06337340B1

Reaction notes

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