Water → HCID 33240185, compound

HRID 1027478Notes

Reaction equation

HRID 1027478 reaction equation
C(N(CC)CC)C.Cl.[CH2:9]([O:11][C:12](=[O:20])[CH:13]([NH2:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:10].[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26].O>ClCCl>[CH2:17]([O:16][C:14](=[O:15])[CH:13]([NH:19][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([F:21])[CH:23]=1)[C:12]([O:11][CH2:9][CH3:10])=[O:20])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 743763-Fluorobenzoyl chlorideHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 33240185HCID 33240185, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

36.1 ml of triethylamine were added to a solution of 25 g of aminomalonic acid diethyl ester hydrochloride in 200 ml of dichloromethane with cooling in an ice bath. Then a solution of 18.7 g of 3-fluoro-benzoyl chloride in 100 ml of dichloromethane was added dropwise. After stirring for 2 h at 0° C., 100 ml of water were added dropwise. The layers were separated, and the aqueous layer was extracted with 100 ml of dichloromethane. The combined organic layers were dried with magnesium sulfate, filtered and evaporated to give 33.2 g of the crude title compound.

Workup

  1. temperaturewith cooling in an ice bath
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 100 ml of dichloromethane
  4. dry with materialThe combined organic layers were dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ebf9bae0f01946c8878fe652c69c9b5e
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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