Dicyclohexylcarbodiimide → HCID 178479428, compound

HRID 703376Notes

Reaction equation

HRID 703376 reaction equation
[ClH:1].[NH:2]([CH2:6][CH2:7][CH2:8][CH2:9][C@H:10](O)[CH2:11][C:12]([NH2:14])=[O:13])[C:3]([NH2:5])=[NH:4].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.[Cu](Cl)Cl>[ClH:1].[NH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH:11][C:12]([NH2:14])=[O:13])[C:3]([NH2:5])=[NH:4]

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 178479440HCID 178479440, compound

Product 1

HCID 178479428HCID 178479428, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 955 mg (4mmoles) of (S)-7-guanidino-3-hydroxyheptanamide hydrochloride in 20 ml of anhydrous N,N-dimethylformamide were added 2.48 g (12 mmoles) of dicyclohexylcarbodiimide and 40 mg of copper(II) chloride. The mixture was stirred for 2 days at room temperature. The reaction mixture was filtered to remove the precipitate and the filtrate was concentrated under reduced pressure. The residue was dissolved in 10 ml of water and washed twice with 10 ml of ethyl acetate. The aqueous layer was evaporated to dryness, dissolved in 5 ml of water, passed through a column (20 mm inner diameter) packed with 50 ml of CM-Sephadex® C-25 (Na-type) and the column was eluted with 200 ml of 0.5M aqueous sodium chloride solution (10 ml fraction size). Fractions No. 17 to No. 30 were combined, evaporated to dryness and extracted 3 times with methanol. The methanol solution was passed through a column (20 mm inner diameter) packed with 150 ml of Sephadex® LH-20 and developed with methanol (5 ml fraction size). Fractions No. 9 to No. 16 were combined and evaporated to dryness. The residue, weighing 950 mg, was crystallized from ethanol-acetone to obtain 790 mg (89.5% yield) of 7-guanidino-2-heptenamide hydrochloride having a melting point of 162°-168° C. Proton NMR (measured in deuteromethanol), δ: 1.4-1.8 (CH2 ×2); 2.27 (CH2); 3.20 (CH2); 5.98 (CH); 6.80 (CH).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the precipitate
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in 10 ml of water
  5. washwashed twice with 10 ml of ethyl acetate
  6. customThe aqueous layer was evaporated to dryness
  7. dissolutiondissolved in 5 ml of water
  8. wash(Na-type) and the column was eluted with 200 ml of 0.5M aqueous sodium chloride solution (10 ml fraction size)
  9. customevaporated to dryness
  10. extractionextracted 3 times with methanol
  11. customevaporated to dryness
  12. customwas crystallized from ethanol-acetone

Sources & evidence

ORD record
ord-6825ba1caaf54e49aeedf71e8ef261d9
Source dataset
uspto-grants-1991_01
Patent number
US04983328

Reaction notes

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