Hydrochloric Acid → HCID 54388748, compound

HRID 1376854Notes

Reaction equation

HRID 1376854 reaction equation
[O:1]=[C:2]([CH:6]=[CH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:3]([OH:5])=[O:4].O1[CH2:18][CH2:17][CH2:16]C1.Cl.[OH-].[Na+].[CH3:22]COCC>>[O:1]=[C:2]([CH:6]=[CH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:3]([O:5][C:17]([CH3:16])([CH3:18])[CH3:22])=[O:4]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 54278194HCID 54278194, compound

Product 1

HCID 54388748HCID 54388748, compound

Conditions

Temperature
20 °C

Procedure

A mixture of 1.41 g of the acid of Step A, 4.5 g of 0-tert.-butyl-N,N-diisopropyl-isourea and 32 ml of tetrahydrofuran was stirred at 20° C. under nitrogen for 15 hours and then 8 ml of aqueous N hydrochloric acid were added with stirring. 8 ml of aqueous N sodium hydroxide solution and 10 ml of ether were added with stirring and the mixture was filtered. The decanted aqueous phase was extracted with ether and the combined organic phases were washed and evaporated to dryness under reduced pressure. The residue was chromatographed over silica and was eluted with a 93-7 methylene chloride-acetone mixture to obtain 1.35 g of 1,1-dimethyl-ethyl 2-oxo-4-{pyridin-3-yl)-3-butenoate melting at 51°-52° C.

Workup

  1. stirringwith stirring
  2. stirringwith stirring
  3. filtrationthe mixture was filtered
  4. extractionThe decanted aqueous phase was extracted with ether
  5. washthe combined organic phases were washed
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was chromatographed over silica
  8. washwas eluted with a 93-7 methylene chloride-acetone mixture

Sources & evidence

ORD record
ord-f6d6f28b4b9c4d119df96783e1a54268
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

Loading…