Ethyl Acetate → HCID 25214746, compound

HRID 2060924Notes

Reaction equation

HRID 2060924 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.N1CC[CH2:23][C@H:19]1[C:20](O)=[O:21].[NH4+].[Cl-].C(OCC)(=[O:30])C>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:17]=[CH:16][C:13]([CH:14]([OH:15])[CH:20]([OH:21])[C:19](=[O:30])[CH3:23])=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 145742L-ProlineHCID 119843244-(1,3-Benzoxazol-2-yl)benzaldehyde

Product 1

HCID 25214746HCID 25214746, compoundYield 66%

Procedure

Flame dried 10 mL flask was filled with argon and charged with hydroxyacetone (1 ml) and anhydrous DMSO (2 ml). After solution is formed the 4-benzoxazol-2-yl-benzaldehyde (2.2 mmol) followed by L-Proline (1.1 mmol) were added. The resulted homogeneous reaction mixture was stirred at room temperature for 24 h. Then, half saturated NH4Cl solution (20 ml) and ethyl acetate (10 ml) was added with vigorous stirring, the layers were separated and the aqueous phase was extracted thoroughly with ethyl acetate (5×10 ml). The combined organic phases were dried (Na2SO4) and concentrated in vacuum. The residue was recrystallized from EtOH yielding 95 mg of pure product as white crystals; the mother liquor was purified by column chromatography (eluent-ethyl acetate/hexanes-6/3) yielding next 125 mg (total yield 66%) of the pure product.

Workup

  1. temperatureFlame
  2. customdried 10 mL flask
  3. additionwas filled with argon
  4. additioncharged with hydroxyacetone (1 ml) and anhydrous DMSO (2 ml)
  5. additionwere added
  6. customthe layers were separated
  7. extractionthe aqueous phase was extracted thoroughly with ethyl acetate (5×10 ml)
  8. dry with materialThe combined organic phases were dried (Na2SO4)
  9. concentrationconcentrated in vacuum
  10. customThe residue was recrystallized from EtOH yielding 95 mg of pure product as white crystals
  11. customthe mother liquor was purified by column chromatography (eluent-ethyl acetate/hexanes-6/3)
  12. customyielding next 125 mg (total yield 66%) of the pure product

Sources & evidence

ORD record
ord-f950ea7ac87342efb7fc17eb7964df60
Source dataset
uspto-grants-2012_10
Patent number
US08278459B2

Reaction notes

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