Oxalic Acid → HCID 67355904, compound

HRID 1930768Notes

Reaction equation

HRID 1930768 reaction equation
CC(C)(C)C([NH:5][C:6]1[C:11]([C:12]2[O:16][N:15]=[C:14]([C:17](OCC)=[O:18])[CH:13]=2)=[CH:10][CH:9]=[CH:8][N:7]=1)=O.[BH4-].[Na+].[OH-].[Na+].[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30]>COC(C)(C)C.O1CCCC1.O.C(O)C>[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30].[NH2:5][C:6]1[C:11]([C:12]2[O:16][N:15]=[C:14]([CH2:17][OH:18])[CH:13]=2)=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

9

Reactant 4

HCID 971Oxalic AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 57867419HCID 57867419, compound

Product 1

HCID 67355904HCID 67355904, compoundYield 69.3%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a mixture of ethyl 5-{2-[(2,2-dimethylpropanoyl)amino]pyridin-3-yl}isoxazol-3-carboxylate (3.17 g, 10 mmol), ethanol (3 mL) and tetrahydrofuran (10 mL) was added sodium borohydride (0.38 g, 10 mmol) at room temperature, which was stirred overnight under a ice cooling to room temperature. The reaction mixture was divided equally into five, among which one was added to 5N aqueous sodium hydroxide (2 mL), which was stirred overnight at 55° C. To the reaction mixture was added water, which was extracted with a mixture of methyl-tert-butylether and tetrahydrofuran, and oxalic acid (0.18 g, 2 mmol) was added to the organic layer. The precipitated solid was filtered to obtain the title compound (0.39 g) as a white solid.

Workup

  1. stirringwas stirred overnight at 55° C
  2. additionwas added to the organic layer
  3. filtrationThe precipitated solid was filtered

Sources & evidence

ORD record
ord-89c62244d6d64209a2eac46a4995b632
Source dataset
uspto-grants-2012_05
Patent number
US08188119B2

Reaction notes

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