Dimethylformamide dimethyl acetal → HCID 68880480, compound

HRID 2111017Notes

Reaction equation

HRID 2111017 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:23])[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:10][CH:9]=1.CO[CH:27](OC)[N:28](C)C.Cl.NO>>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:23][N:28]=[CH:27][C:15]=2[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 443297Hydroxyamine hydrochlorideHCID 68884452HCID 68884452, compound

Product 1

HCID 68880480HCID 68880480, compoundYield 65%

Conditions

Temperature
100 °C

Procedure

To tert-butyl 3-(4-{[(3-methoxy-3-oxopropyl)thio]methyl}phenyl)-3-oxopropionate (472 mg, 1.34 mmol) was added N,N-dimethylformamide dimethylacetal (5 ml), and the mixture was stirred at 100° C. for 1 hour. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethanol (10 ml). Hydroxylamine hydrochloride (280 mg, 4.03 mmol) was added, and the mixture was stirred at 70° C. for 2 hours. The solvent was evaporated under reduced pressure and water was added. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to give the title compound (330 mg, 65%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethanol (10 ml)
  3. stirringthe mixture was stirred at 70° C. for 2 hours
  4. customThe solvent was evaporated under reduced pressure and water
  5. additionwas added
  6. extractionThe mixture was extracted with ethyl acetate
  7. washthe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe obtained crude product
  11. customwas purified by silica gel chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-63d2508f024d4f94b2f480321bc16abe
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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