Hydrochloric Acid → 1186526-25-9

HRID 2368643Notes

Reaction equation

HRID 2368643 reaction equation
[C:1]([OH:7])(=O)[CH2:2][C:3]([OH:5])=[O:4].[CH2:8]([K])[CH3:9].[Cl-].[Mg+2].[Cl-].N1([C:19](=O)[CH:20]([O:22][CH3:23])C)C=CN=C1.COC(C)C(O)=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl>C(#N)C.C(N(CC)CC)C>[CH2:8]([O:5][C:3](=[O:4])[CH2:2][C:1](=[O:7])[CH:20]([O:22][CH3:23])[CH3:19])[CH3:9]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 922092-Methoxypropanoic acidHCID 5360315Magnesium ChlorideHCID 66862569HCID 66862569, compoundHCID 178461627HCID 178461627, compound

Product 1

HCID 581197321186526-25-9

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent3×HCID 8471TriethylamineSolvent

Procedure

89 g ethyl potassium malonate are dissolved in 700 ml acetonitrile. While being stirred 109 ml triethylamine and 60 g magnesium chloride are added and the mixture is stirred for 2 hours. Then a solution of 1-imidazol-1-yl-2-methoxy-propan-1-one in 150 ml acetonitrile, prepared by mixing 27 g 2-methoxypropionic acid and 48 g carbonyldiimidazol in acetonitrile and stirring for 12 hours, is added and stirring is continued for 12 hours. 1 l of a 13% solution of hydrochloric acid is added while keeping the temperature below 25° C. and the mixture is stirred for 10 minutes. The phases are separated and the aqueous phase is extracted three times with ethylacetate. The combined organic phases are washed with saturated aqueous sodium bicarbonate and brine. After drying with magnesium sulphate the solvents are evaporated. The crude product is used directly in the next step.

Workup

  1. additionare added
  2. stirringstirring for 12 hours
  3. additionis added
  4. stirringstirring
  5. waitis continued for 12 hours
  6. customthe temperature below 25° C.
  7. stirringthe mixture is stirred for 10 minutes
  8. customThe phases are separated
  9. extractionthe aqueous phase is extracted three times with ethylacetate
  10. washThe combined organic phases are washed with saturated aqueous sodium bicarbonate and brine
  11. dry with materialAfter drying with magnesium sulphate the solvents
  12. customare evaporated

Sources & evidence

ORD record
ord-5589726d4c9d469b80d9ef6ea512e25b
Source dataset
uspto-grants-2014_04
Patent number
US08703793B2

Reaction notes

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