Methyl cyanoacetate → HCID 178437791, compound

HRID 531112Notes

Reaction equation

HRID 531112 reaction equation
CO[CH:3]([O:7]C)[N:4]([CH3:6])C.O=C(CC)[CH2:11][C:12]([O:14][CH3:15])=[O:13].[C:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])#N.[CH2:25](N(C(C)C)C(C)C)[CH3:26]>CO.O.C(O)(=O)C>[CH2:25]([C:6]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:18][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:3]([OH:7])[N:4]=1)[CH3:26]

Participants

8

Reactant 4

HCID 7747Methyl cyanoacetateHCID 78373Dimethylformamide dimethyl acetalHCID 81531DiisopropylethylamineHCID 121699Methyl 3-oxovalerate

Product 1

HCID 178437791HCID 178437791, compoundYield 47.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1,1-Dimethoxy-N,N-dimethylmethanamine (24.4 g) was added to a solution of methyl 3-oxopentanoate (25.4 g) in methanol (50 mL) at room temperature. The mixture was stirred at 50° C. under nitrogen atmosphere for 3 hours. After cooling to room temperature, methyl cyanoacetate (21.3 g) and N-ethyl-N-isopropylpropan-2-amine (25.2 g) were added to the reaction mixture. The mixture was stirred at 50° C. under nitrogen atmosphere for 16 hours. After cooling to room temperature, acetic acid (14.1 g) was added to the reaction mixture at 50° C. The mixture was stirred at 50° C. under nitrogen atmosphere for 10 minutes. Water (150 mL) was added to the reaction mixture at 50° C. The mixture was stirred at room temperature for 2 hours. After filtration, the crystals were washed with methanol-water (1:4) and then diisopropyl ether. The crystals were dried at 70° C. under vacuum to give the title compound (22.3 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringThe mixture was stirred at 50° C. under nitrogen atmosphere for 16 hours
  3. temperatureAfter cooling to room temperature
  4. stirringThe mixture was stirred at 50° C. under nitrogen atmosphere for 10 minutes
  5. stirringThe mixture was stirred at room temperature for 2 hours
  6. filtrationAfter filtration
  7. washthe crystals were washed with methanol-water (1:4)
  8. customThe crystals were dried at 70° C. under vacuum

Sources & evidence

ORD record
ord-f457e76bcbba4d9a83f1272bd931ef59
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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