Water → HCID 549238, compound

HRID 1481043Notes

Reaction equation

HRID 1481043 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].[CH2:8]1CCN2C(=NCCC2)C[CH2:9]1.ICC.O>CN(C=O)C.CCOC(C)=O>[C:1]([CH:3]([CH2:8][CH3:9])[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 7747Methyl cyanoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 549238HCID 549238, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 2-cyanoacetate (2.0 mL, 22.61 mmol., Acros) and DBU (3.4 mL, 22.61 mmol) in DMF (22 mL) was added iodoethane (2.0 mL, 24.90 mmol) dropwise at 0° C. The resulting mixture was heated to 70° C. for 20 hours. After cooling to room temperature, H2O (150 mL) and EtOAc (150 mL) were added. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-30% EtOAc/hexanes) to give the title compound in 300 mg. 1H NMR (CDCl3, 200 MHz): δ=3.82 (s, 3H), 3.48 (dd, 1H, J=5.9 Hz and 6.8 Hz), 2.08-1.92 (m, 2H), 1.12 (t, 3H, J=7.3 Hz).

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d57991e9c00848a3ab447cd6c595788a
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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