Hydrochloric Acid → HCID 22351163, compound

HRID 896589Notes

Reaction equation

HRID 896589 reaction equation
C(O[N:5]1[C:9]([CH3:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8](=[O:17])[N:7]([C:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])[C:6]1=[O:30])(=O)C.Cl.F[C:33](F)(F)[C:34]([OH:36])=[O:35].ClCCl>>[CH3:16][C:9]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:5]([CH2:33][C:34]([OH:36])=[O:35])[C:6](=[O:30])[N:7]([C:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])[C:8]1=[O:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 21863450Trifluoroacetic acid methylene chlorideHCID 69732989HCID 69732989, compound

Product 1

HCID 22351163HCID 22351163, compound

Procedure

Tert-butyl (5-methyl-3-naphthylcarbonyl-2,4-dioxo-5-phenylimidazolidinyl acetate (400 mg) was dissolved in a 20% trifluoroacetic acid/dichloromethane solution (10 mL), and the mixture was stirred at room temperature overnight. After 0.5N hydrochloric acid was added, and the solution was extracted twice using chloroform (100 mL). The resulting organic layer was washed with a saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. Further recrystallization from IPE afforded 276 mg of white crystals.

Workup

  1. extractionthe solution was extracted twice using chloroform (100 mL)
  2. washThe resulting organic layer was washed with a saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customFurther recrystallization from IPE afforded 276 mg of white crystals

Sources & evidence

ORD record
ord-829b607985da4f2db91009a76d5071a5
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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