Water → HCID 58537227, compound

HRID 1804491Notes

Reaction equation

HRID 1804491 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([C:16]([O:18]C)=[O:17])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[Li+].[OH-]>CO>[CH3:15][O:14][C:12]([C:11]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:8][O:9][C:10]=1[C:16]([OH:18])=[O:17])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 608690Dimethyl 3-phenyl-4,5-isoxazoledicarboxylate

Product 1

HCID 58537227HCID 58537227, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of dimethyl 3-phenylisoxazole-4,5-dicarboxylate (770 mg, 2.95 mmol) in MeOH (15 mL)/water (5.00 mL) at rt was added LiOH, hydrate (124 mg, 2.95 mmol) and the reaction mixture was allowed to stir at rt for 1 hr. The MeOH was removed in vacuo and the remaining aqueous solution was diluted with water (5 mL). The pH was adjusted to <1 with 1N HCl and the mixture was extracted with EtOAc (40 mL). The organic layer was washed with brine (25 mL), dried (MgSO4) and concentrated to afford 4-(methoxycarbonyl)-3-phenylisoxazole-5-carboxylic acid (709 mg, 2.87 mmol, 97% yield) as a colorless oil. HPLC retention time=1.99 minutes (YMC Combi 4.6×50 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.2% phosphoric acid over a 4 minute gradient. MS: (M+H)=248.13. 1H NMR (400 MHz, chloroform-d) δ ppm 3.89 (s, 3H) 7.51 (m, 5H).

Workup

  1. customThe MeOH was removed in vacuo
  2. additionthe remaining aqueous solution was diluted with water (5 mL)
  3. extractionthe mixture was extracted with EtOAc (40 mL)
  4. washThe organic layer was washed with brine (25 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2a7ab3937a8a489b89d8512220bef702
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

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