Guanidine → HCID 178422469, compound

HRID 2290392Notes

Reaction equation

HRID 2290392 reaction equation
[NH2:1][C:2]([NH2:4])=[NH:3].Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[C:12]([NH:16][C:17]([CH:19]1[CH2:21][C:20]1([CH3:23])[CH3:22])=[O:18])[C:13]([OH:15])=[O:14]>O>[CH3:22][C:20]1([CH3:23])[CH2:21][CH:19]1[C:17]([NH:16]/[C:12](=[CH:11]\[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:3][C:2]([NH2:4])=[NH:1])/[C:13]([OH:15])=[O:14])=[O:18]

Participants

4

Reactant 2

HCID 3520GuanidineHCID 54449392HCID 54449392, compound

Product 1

HCID 178422469HCID 178422469, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2 mmoles of guanidine (prepared from 432 mg of guanidine sulfate and 630 mg of barium hydroxide octahydrate) in 7 ml of water was added 332 mg (1 mmole) of 8-bromo-2-(2,2-dimethylcyclopropanecarboxamido)-2-octenoic acid, and the solution was heated at 70° C. in a nitrogen atmosphere for 1 hr. The reaction mixture was applied to a 2×25 cm column of Dowex 50W-X8 (H+, 100-200 mesh). After elution with water the fractions containing the product were pooled and evaporated under reduced pressure. The residue was dissolved in several ml of warm ethanol and added dropwise to 100 ml of ether with rapid stirring. Filtration and washing with ether gave 107 mg of Z-2-(2,2-dimethylcyclopropanecarboxamido)-8-guanidino-2-octenoic acid as an amorphous electrostatic powder. Homogeneous by TLC (n-BuOH, HOAc, H2O; 4:1:1). NMR (D2O, NaOD): ##STR72##

Workup

  1. washAfter elution with water the fractions
  2. additioncontaining the product
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in several ml of warm ethanol
  5. additionadded dropwise to 100 ml of ether with rapid stirring
  6. filtrationFiltration
  7. washwashing with ether

Sources & evidence

ORD record
ord-88f5f23aa3954f6db27329446964c4bd
Source dataset
uspto-grants-1986_10
Patent number
US04616038

Reaction notes

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