Diisopropylcarbodiimide → HCID 63383281, compound

HRID 1409368Notes

Reaction equation

HRID 1409368 reaction equation
[NH2:1][C:2](=[N:8][OH:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[O:10]1[CH:14]=[CH:13][C:12]([C:15](O)=O)=[N:11]1.C(N=C=NC(C)C)(C)C>C(Cl)Cl>[O:10]1[CH:14]=[CH:13][C:12]([C:15]2[O:9][N:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:1]=2)=[N:11]1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetateHCID 112864533-Isoxazolecarboxylic acid

Product 1

HCID 63383281HCID 63383281, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl aminohydroxyiminoacetate (3.78 mmol, 0.5 g), 3-isoxazolecarboxylic acid (3.78 mmol, 0.428 g) and 1,3-diisopropylcarbodiimide (4.16 mmol, 0.525 g) were dissolved in DCM (70 ml) under nitrogen atmosphere. The mixture was stirred at RT for a day. The solvent was evaporated to dryness and the residue was dissolved in pyridine and refluxed for 6 h and overnight at RT. Pyridine was evaporated and the residue was diluted with DCM and water. The aqueous phase was extracted four times with DCM. The combined organics were washed with aqueous HCl solution, saturated NaHCO3, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.396 g of the title compound was obtained. Rotamers were obtained in 1H-NMR and analysis was repeated at elevated temperature. 1H-NMR (400 MHz, DMSO-d6, +60° C.): δ 1.38 (t, 3H), 4.49 (q, 2H), 7.21 (d, 1H), 9.05 (d, 1H).

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionthe residue was dissolved in pyridine
  3. temperaturerefluxed for 6 h and overnight at RT
  4. customPyridine was evaporated
  5. additionthe residue was diluted with DCM and water
  6. extractionThe aqueous phase was extracted four times with DCM
  7. washThe combined organics were washed with aqueous HCl solution, saturated NaHCO3, water and brine
  8. customThe organic phase was dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-d04a6c07498740cdb0b7cbee195d020f
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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