Citric Acid → HCID 22325074, compound

HRID 496057Notes

Reaction equation

HRID 496057 reaction equation
C[Si](Cl)(C)C.[OH:6][C:7]1([C:10]([OH:12])=O)[CH2:9][CH2:8]1.C(Cl)(=O)C(Cl)=O.[CH3:19][NH:20][CH3:21].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.N1C=CC=CC=1.CN(C)C=O.CO>[OH:6][C:7]1([C:10]([N:20]([CH3:21])[CH3:19])=[O:12])[CH2:9][CH2:8]1

Participants

10

Reactant 5

HCID 311Citric AcidHCID 674DimethylamineHCID 6397ChlorotrimethylsilaneHCID 65578Oxalyl chlorideHCID 27331601-Hydroxy-1-cyclopropanecarboxylic acid

Product 1

HCID 22325074HCID 22325074, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 887MethanolSolventHCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

17.1 ml of trimethylsilyl chloride are added dropwise to a solution of 6 g of 1-hydroxy-cyclopropanecarboxylic acid in 120 ml of dichloromethane and 10.5 ml of pyridine. After stirring for 4 hours at ambient temperature, the mixture is cooled to 0° C., and 10 drops of dimethylformamide and then 5.4 ml of oxalyl chloride are added. The reaction mixture is stirred at 0° C. for 1 hour and at ambient temperature for 1 hour; a solution of 2.4 g of dimethylamine in 10 ml of pyridine is then added. Stirring is continued for 20 hours and then, after cooling to 0° C., 14 g of citric acid in 120 ml of methanol are added. After returning to ambient temperature for one hour, the reaction mixture is washed with 1N hydrochloric acid solution and then with NaHCO3-saturated solution and then NaCl-saturated solution. The organic phase is treated in conventional manner and chromatography over silica gel (dichloromethane/tetrahydrofuran: 90/10) allows the expected product to be isolated.

Workup

  1. temperaturethe mixture is cooled to 0° C.
  2. stirringThe reaction mixture is stirred at 0° C. for 1 hour and at ambient temperature for 1 hour
  3. stirringStirring
  4. waitis continued for 20 hours
  5. temperatureafter cooling to 0° C.
  6. waitAfter returning to ambient temperature for one hour
  7. washthe reaction mixture is washed with 1N hydrochloric acid solution
  8. additionThe organic phase is treated in conventional manner and chromatography over silica gel (dichloromethane/tetrahydrofuran: 90/10)
  9. customto be isolated

Sources & evidence

ORD record
ord-e6897dd723d3420e992e156c184c155e
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Reaction notes

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