Diethyl Ether → HCID 67247790, compound

HRID 2425325Notes

Reaction equation

HRID 2425325 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14]C)=[O:12])[C:6]([O:8][CH2:9]C)=[O:7])(=[O:3])[CH3:2].[H-].[Na+].[CH2:18]([C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[C:31](=[CH2:35])[C:30](=[O:36])[CH2:29]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].CCOCC>C1COCC1.O>[CH3:14][O:13][C:11](=[O:12])[C:5]([NH:4][C:1](=[O:3])[CH3:2])([CH2:35][CH:31]1[C:32]2[C:28](=[CH:27][C:26]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:34][CH:33]=2)[CH2:29][C:30]1=[O:36])[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydrideHCID 67247928HCID 67247928, compound

Product 1

HCID 67247790HCID 67247790, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl acetamidomalonate (4.55 g, 21.0 mmol) is dissolved in THF (40 mL). Sodium hydride (0.600 g, 25.0 mmol) is added. The reaction is brought to reflux for 2.0 hours. The residue (compound 16) from Example 12, dissolved in THF (40 mL) is added. The reaction is maintained at reflux for an additional 4 hours, cooled, and poured into a separatory funnel containing ether (100 mL) and water (75 mL). The ether layer is separated and the aqueous layer is re-extracted with ether (100 mL). The combined organic layers are dried over MgSO4 and the solvent removed in vacuo. The residue is chromatographed over silica gel yielding 17 (FIG. 7).

Workup

  1. temperatureto reflux for 2.0 hours
  2. additionis added
  3. temperatureThe reaction is maintained
  4. temperatureat reflux for an additional 4 hours
  5. temperaturecooled
  6. additionpoured into a separatory funnel
  7. customThe ether layer is separated
  8. extractionthe aqueous layer is re-extracted with ether (100 mL)
  9. dry with materialThe combined organic layers are dried over MgSO4
  10. customthe solvent removed in vacuo
  11. customThe residue is chromatographed over silica gel yielding 17 (FIG. 7)

Sources & evidence

ORD record
ord-9b02fa4e29b142998ee42e509ce32eec
Source dataset
uspto-grants-2011_06
Patent number
US07964649B2

Reaction notes

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