Hydrochloric Acid → HCID 10788402, compound

HRID 1532751Notes

Reaction equation

HRID 1532751 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:33]=[CH:32][C:19]([CH2:20][CH:21]([C:27]([O:29]CC)=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=1.O.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[CH2:25]([O:24][C:22]([CH:21]([CH2:20][C:19]1[CH:32]=[CH:33][C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:17][CH:18]=1)[C:27]([OH:29])=[O:28])=[O:23])[CH3:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 117978601,3-Diethyl 2-[[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]propanedioate

Product 1

HCID 10788402HCID 10788402, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylmalonate (4.60 g, 10.2 mmol) obtained in Example 55 was dissolved in a mixed solvent of ethanol (50 ml) and tetrahydrofuran (25 ml), and the mixture was stirred at room temperature for 18 hr. The solvent was evaporated to give a crude solid. Water (20 ml) and 1N sodium hydroxide (30 ml) were added to dissolve said crude solid. 1N Hydrochloric acid was added at 0° C., and the mixture was extracted three times with ethyl acetate (30 ml). The extracted organic layer was washed with brine, dried over sodium sulfate and concentrated to dryness to give a crude title compound (4.7 g), which was purified and concentrated by silica gel column chromatography (developing solvent; chloroform:methanol=100:1→50:1) to give the title compound. This compound was dissolved in 1N sodium hydroxide (10 ml) and washed twice with ethyl acetate (30 ml). 1N Hydrochloric acid (15 ml) was added to the aqueous layer, and the mixture was extracted three times with ethyl acetate (30 ml). The extracted organic layer was washed with brine, dried over sodium sulfate and concentrated to dryness to give the title compound (2.91 g, yield 67%) as white crystals.

Workup

  1. customThe solvent was evaporated
  2. customto give a crude solid
  3. dissolutionto dissolve
  4. extractionthe mixture was extracted three times with ethyl acetate (30 ml)
  5. washThe extracted organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness
  8. customto give a crude title compound (4.7 g), which
  9. customwas purified
  10. concentrationconcentrated by silica gel column chromatography (developing solvent; chloroform:methanol=100:1→50:1)

Sources & evidence

ORD record
ord-54c7a1c2917e4d43a39d088c40f7b553
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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