Hydrochloric Acid → HCID 19434039, compound

HRID 1736038Notes

Reaction equation

HRID 1736038 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]([S:8]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[CH:16]1OCCO1)(=[O:10])=[O:9])[CH3:7])[CH3:2].FC(F)(F)C(O)=O.C1CN2C(=NCCC2)C1.Cl>CC(C)=O.C(OCC)(=O)C.O>[CH3:7][N:6]1[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:21])=[CH:16][C:12]2[S:13][CH:14]=[CH:15][C:11]=2[S:8]1(=[O:10])=[O:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 19434099HCID 19434099, compound

Product 1

HCID 19434039HCID 19434039, compoundYield 79.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from Step C (5.86 g, 16.5 mmol) and trifluoroacetic acid (8 mL) in acetone (50 mL) was heated at reflux temperature for 1 h, cooled, and poured into water (100 mL). Acetone was evaporated and the aqueous was combined with a saturated aqueous solution of sodium bicarbonate (50 mL) and this mixture was extracted with ethyl acetate (2×150 mL). The combined extracts were dried (MgSO4) and evaporated to give a crude aldehyde which was dissolved in ethyl acetate (100 mL) followed by the addition of DBN (1 mL) and molecular sieves (5 g). This mixture was heated at reflux temperature for 15 min, cooled, and poured into 2N HCl (50 mL). The organic layer was separated, dried (MgSO4), and evaporated to dryness. Column chromatography (silica, 30% ethyl acetate/hexane) gave 3.60 g (79%) of an off-white solid: mp 87°-89° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 h
  3. temperaturecooled
  4. customAcetone was evaporated
  5. extractionthis mixture was extracted with ethyl acetate (2×150 mL)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customevaporated
  8. customto give a crude aldehyde which
  9. temperatureThis mixture was heated
  10. temperatureat reflux temperature for 15 min
  11. temperaturecooled
  12. customThe organic layer was separated
  13. dry with materialdried (MgSO4)
  14. customevaporated to dryness

Sources & evidence

ORD record
ord-e5e98408f6774db0b9f00141575a43b6
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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