Potassium → HCID 178494030, compound

HRID 358849Notes

Reaction equation

HRID 358849 reaction equation
C[C:2](C)([O-:4])C.[K+].C(OC(C1C(C(OCC)=O)=CC(C)=C(COC)N=1)=O)C.NC(C)(C(C)C)C(N)=O.[K].[CH:37]([C:40]1([CH3:57])[NH:44][C:43]([C:45]2[C:50]([C:51]([OH:53])=[O:52])=[CH:49][C:48]([CH2:54]C)=[CH:47][N:46]=2)=[N:42][C:41]1=[O:56])([CH3:39])[CH3:38]>C1(C)C=CC=CC=1>[CH3:2][O:4][C:47]1[N:46]=[C:45]([C:43]2[NH:44][C:40]([CH:37]([CH3:39])[CH3:38])([CH3:57])[C:41](=[O:56])[N:42]=2)[C:50]([C:51]([OH:53])=[O:52])=[CH:49][C:48]=1[CH3:54]

Participants

7

Reactant 5

HCID 5462222PotassiumHCID 97937732-Amino-2,3-dimethylbutanamideHCID 23665647Potassium tert-butoxide2×HCID 53970916HCID 53970916, compoundHCID 178437115HCID 178437115, compound

Product 1

HCID 178494030HCID 178494030, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5 g of potassium tert.-butoxide are added in portions at a temperature of 80° C. to a solution of 5.7 g of 6-methoxymethyl-5-methylpyridine-2,3-dicarboxylic acid diethyl ester and 2.6 g of 2-amino-2,3-dimethylbutyramide in 200 ml of dry toluene while stirring. Once the addition of the potassium tert.-butoxide is complete, the resulting red solution is stirred for 2 hours at 80° C., the potassium salt of 2-(5-isopropyl-5-methyl-4-oxoimidazolin-2-yl)-5-ethylpyridine-3-carboxylic acid being deposited in the form of a thick crystalline slurry. The mixture is cooled to room temperature and filtered with suction, and the crystals are dried and then dissolved in 50 ml of saturated sodium chloride solution. The solution is adjusted to pH 4 with concentrated hydrochloric acid and then extracted three times with 100 ml of ethyl acetate each time. The organic phase is dried over magnesium sulphate, filtered off with suction and concentrated by evaporation. The residue crystallises from ether/hexane 1:2 yielding 2.8 g of the above acid, which has a melting point of 151°-153° C.

Workup

  1. stirringthe resulting red solution is stirred for 2 hours at 80° C.
  2. filtrationfiltered with suction
  3. customthe crystals are dried
  4. dissolutiondissolved in 50 ml of saturated sodium chloride solution
  5. extractionextracted three times with 100 ml of ethyl acetate each time
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. filtrationfiltered off with suction
  8. concentrationconcentrated by evaporation
  9. customThe residue crystallises from ether/hexane 1:2 yielding 2.8 g of the above acid, which

Sources & evidence

ORD record
ord-74e1eea7522a424985bec55ffcbbcc6e
Source dataset
uspto-grants-1991_03
Patent number
US04997947

Reaction notes

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