Sodium Hydroxide → (-)-(3-Isopropyl-5-methyl-2,4-dioxo-5-phenylimidazolin-1-yl)acetic acid

HRID 1685377Notes

Reaction equation

HRID 1685377 reaction equation
[CH:1]([N:4]1[C:8](=[O:9])[C:7]([CH3:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]([CH2:17][C:18]([O:20]C)=[O:19])[C:5]1=[O:22])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[CH:1]([N:4]1[C:8](=[O:9])[C:7]([CH3:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]([CH2:17][C:18]([OH:20])=[O:19])[C:5]1=[O:22])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86642550Methyl (3-isopropyl-5-methyl-2,4-dioxo-5-phenylimidazolin-1-yl)acetate

Product 1

HCID 59370453(-)-(3-Isopropyl-5-methyl-2,4-dioxo-5-phenylimidazolin-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl (3-isopropyl-5-methyl-2,4-dioxo-5-phenylimidazolin-1-yl)acetate, isomer B from Step B (700 mg, 2.3 mmol) in MeOH (20 mL) was added 1 N aqueous NaOH (5.0 mL, 5.0 mmol) and the resulting mixture was stirred at ambient temperature for 18 h. The reaction was quenched by addition of 1 N HCl (5 mL) and the reaction was poured into water (100 mL) and the mixture was adjusted to pH 3 with 1 N HCl. The aqueous mixture was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound. MS: m/z=291 (M+1).

Workup

  1. customThe reaction was quenched by addition of 1 N HCl (5 mL)
  2. additionthe reaction was poured into water (100 mL)
  3. extractionThe aqueous mixture was extracted with EtOAc (2×50 mL)
  4. washThe combined organic extracts were washed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ee93c7bf6d64eccb42da9595759f722
Source dataset
uspto-grants-2012_04
Patent number
US08148390B2

Reaction notes

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