Tetrahydrofuran → Benzyl (2-oxo-1,2-dihydropyridin-3-yl)carbamate

HRID 617638Notes

Reaction equation

HRID 617638 reaction equation
[NH2:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].C1COCC1.[CH2:20]([O:27][C:28](Cl)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C.O1CCOCC1>[CH2:20]([O:27][C:28]([NH:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 3223533-Amino-2-pyridinol

Product 1

HCID 12045578Benzyl (2-oxo-1,2-dihydropyridin-3-yl)carbamateYield 70%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 3-aminopyrid-2-one (24.6 g, 0.223 mol), sodium carbonate (52.1 g, 0.492 mol), THF (250 mL) and 1,4-dioxane (50 mL) was added dropwise benzyloxycarbonyl chloride (35.1 mL, 0.246 mol). The resulting mixture was stirred at room temperature for 15 h. Ethyl acetate (1200 mL) was added and the mixture was washed with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine. After filtering off insolubles, the filtrate was dried over anhydrous magnesium sulfate. The residue obtained by concentration of the extract solution was recrystallized from methanol-ethyl acetate (6:1) to give 21.5 g of 3-benzyloxycarbonylaminopyrid-2-one as colorless crystals. The insolubles obtained were dissolved in chloroformmethanol (10:1), and then washed with saturated brine. The aqueous layer was further extracted with chloroform, and combined with the organic layer obtained earlier. The combined extracts were dried over anhydrous magnesium sulfate. Evaporation of the solvent further afforded 16.7 g (total yield 70%) of the same product as a colorless solid.

Workup

  1. washthe mixture was washed with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  2. filtrationAfter filtering off insolubles
  3. dry with materialthe filtrate was dried over anhydrous magnesium sulfate
  4. customThe residue obtained by concentration of the extract solution
  5. customwas recrystallized from methanol-ethyl acetate (6:1)

Sources & evidence

ORD record
ord-cd3408f1bef14e81a916ab3faf8b0eb2
Source dataset
uspto-grants-1999_09
Patent number
US05948785

Reaction notes

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