Water → HCID 22626917, compound

HRID 1672092Notes

Reaction equation

HRID 1672092 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:22])[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][N:13]2[CH3:16])=[CH:8][CH:7]=1.O>CC(C)=O>[CH:2]([C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:22])[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][N:13]2[CH3:16])=[CH:8][CH:7]=1)=[O:1]

Participants

4

Reactant 2

HCID 962WaterHCID 59861579HCID 59861579, compound

Product 1

HCID 22626917HCID 22626917, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Compound 9 was dissolved in acetone (EMCO), at 60° C. in a 1 L, 1-neck round bottom flask. Pre-washed Amberlite IR-120 resin (Aldrich) was added with the water and the mixture was stirred at 60° C. for 40 minutes; aliquots were removed at 20 min (MCLS0995-078-1) and 40 min. HPLC analysis of the aliquots revealed that the de-protection of the aldehyde was complete in 20 minutes. The mixture was removed from the heating bath, filtered, and concentrated to ca. 40% of the initial volume under rotary evaporation (removal of acetone). The resulting aqueous suspension was partitioned between CH2Cl2 and sat. aq. sodium bicarbonate. The aqueous layer was extracted 2×CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford product 10 (4.20 g, 81% yield).

Workup

  1. customaliquots were removed at 20 min (MCLS0995-078-1) and 40 min
  2. waitwas complete in 20 minutes
  3. customThe mixture was removed from the heating bath
  4. filtrationfiltered
  5. concentrationconcentrated to ca. 40% of the initial volume
  6. customunder rotary evaporation (removal of acetone)
  7. customThe resulting aqueous suspension was partitioned between CH2Cl2 and sat. aq. sodium bicarbonate
  8. extractionThe aqueous layer was extracted 2×CH2Cl2
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-a736ec6fa78d497f915f889d8e922ba2
Source dataset
uspto-grants-2011_08
Patent number
US07998462B2

Reaction notes

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