Hydrochloric Acid → HCID 57329643, compound

HRID 1644770Notes

Reaction equation

HRID 1644770 reaction equation
Cl.C([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12](=[O:23])[NH:13][C:14]2[S:15][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][N:18]=2)[CH:7]=1)(=O)C>O1CCCC1>[OH:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[C:12]([NH:13][C:14]1[S:15][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][N:18]=1)=[O:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57329641HCID 57329641, compound

Product 1

HCID 57329643HCID 57329643, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 M hydrochloric acid (40.0 mL) was added to a suspension of 79 (0.370 g, 1.09 mmol) in tetrahydrofuran (17.0 mL), and the reaction was warmed to reflux. The reaction became homogeneous upon heating. After refluxing for 4 hours, the reaction was allowed to cool to room temperature, and concentrated in vacuo. The residue was suspended in water and filtered. The filter pad was washed with water, air dried, and then re-dissolved in a minimum amount of warm THF. Water was added to the warm THF solution until the solution turned turbid, and the resulting mixture was allowed to cool to room temperature. Additional water was added, and a white solid formed on standing. The crystalline product was filtered, and the filter pad was washed with water, and dried in vacuo at 70° C. to give 81 (0.182 g, 56%) as a white crystalline solid.

Workup

  1. temperaturethe reaction was warmed to reflux
  2. temperatureupon heating
  3. temperatureAfter refluxing for 4 hours
  4. concentrationconcentrated in vacuo
  5. filtrationfiltered
  6. washThe filter pad was washed with water, air
  7. customdried
  8. dissolutionre-dissolved in a minimum amount of warm THF
  9. additionWater was added to the warm THF solution until the solution
  10. temperatureto cool to room temperature
  11. additionAdditional water was added
  12. customa white solid formed
  13. filtrationThe crystalline product was filtered
  14. washthe filter pad was washed with water
  15. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-fd3ce567a58c447ca48400e7400b4c1c
Source dataset
uspto-grants-2012_02
Patent number
US08124632B2

Reaction notes

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