Hydrochloric Acid → HCID 178474811, compound

HRID 274219Notes

Reaction equation

HRID 274219 reaction equation
C1(N=C=N[CH:10]2[CH2:15]CCCC2)CCCCC1.Cl.[NH2:17][CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[NH:27]([CH2:31][CH2:32][CH2:33][C@@H:34]1[NH:38][C:37](=[O:39])[N:36](CC(O)=O)[C:35]1=[O:44])[C:28]([NH2:30])=[NH:29].C1C=CC2N([OH:54])N=NC=2C=1>CN(C)C=O>[C:23]([O:22][C:20](=[O:21])[CH2:19][CH2:18][N:17]([N:36]1[C:35](=[O:44])[C@H:34]([CH2:33][CH2:32][CH2:31][NH:27][C:28]([NH2:30])=[NH:29])[NH:38][C:37]1=[O:39])[C:15](=[O:54])[CH3:10])([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 4192171tert-Butyl 3-aminopropanoateHCID 178512834HCID 178512834, compound

Product 1

HCID 178474811HCID 178474811, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

0.88 g of dicyclohexylcarbodiimide are added to a suspension of 0.73 g of HCl.H-β-Ala-OtBu, 1.03 g of [5-(S)-(3-guanidinopropyl)-2,4-dioxoimidazolidin-3-yl]-acetic acid and 0.54 g of HOBt in 30 ml of dimethylformamide at 0° C. The mixture is stirred at 0° C. for one hour and at room temperature for 3 hours. It is then left to stand at room temperature overnight, and the insoluble material is filtered off with suction. The filtrate is concentrated, and the residue is chromatographed over ®Sephadex LH20 in a mixture of glacial acetic acid, butanol and water. The fractions containing the pure substance are concentrated, the residue is dissolved in water and the product is freeze-dried.

Workup

  1. customat 0° C
  2. waitIt is then left
  3. waitto stand at room temperature overnight
  4. filtrationthe insoluble material is filtered off with suction
  5. concentrationThe filtrate is concentrated
  6. customthe residue is chromatographed over ®Sephadex LH20 in a mixture of glacial acetic acid, butanol and water
  7. additionThe fractions containing the pure substance
  8. concentrationare concentrated
  9. dissolutionthe residue is dissolved in water
  10. customthe product is freeze-dried

Sources & evidence

ORD record
ord-be4e544585024c6ea2eb5974b3bce34c
Source dataset
uspto-grants-1995_02
Patent number
US05389614

Reaction notes

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