Lithium Hydroxide → (5-Methyl-2,4-dioxo-1,3-thiazolidin-5-yl)acetic acid

HRID 1190830Notes

Reaction equation

HRID 1190830 reaction equation
[CH3:1][C:2]1([CH2:9][C:10]([O:12]C)=[O:11])[S:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[Li+].[OH-]>C1COCC1>[CH3:1][C:2]1([CH2:9][C:10]([OH:12])=[O:11])[S:6][C:5](=[O:7])[NH:4][C:3]1=[O:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86707725Methyl 2-(5-methyl-2,4-dioxothiazolidin-5-yl)acetate

Product 1

HCID 3240161(5-Methyl-2,4-dioxo-1,3-thiazolidin-5-yl)acetic acidYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound 1e (0.18 g, 0.86 mmol) in THF (8 mL) was added 1 M LiOH (2.6 mL, 2.6 mmol) at rt. After 5 h, the organic solvent was evaporated under reduced pressure and the resultant aqueous layer was diluted with water and acidified by the addition of 1 N HCl solution to pH ˜2. The solution was extracted with EtOAc (2×) and the combined extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to afford Compound 1a (150 mg, 92%) as a white solid. LCMS=0.67 min using analytical method (B), 189.9 (M+H). 1H NMR (400 MHz, CD3OD) δ 3.15-2.89 (m, 2H), 1.72 (s, 3H).

Workup

  1. customthe organic solvent was evaporated under reduced pressure
  2. additionthe resultant aqueous layer was diluted with water
  3. additionacidified by the addition of 1 N HCl solution to pH ˜2
  4. extractionThe solution was extracted with EtOAc (2×)
  5. dry with materialthe combined extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-47f1c5b8310542b0b200660bd3e8437b
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

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