HCID 178451103, compound → HCID 178479433, compound

HRID 981329Notes

Reaction equation

HRID 981329 reaction equation
[ClH:1].Cl.C([O:10][CH:11]([NH:29][C:30](=[O:41])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([NH2:40])=[NH:39])[C:12](=[O:28])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])C1C=CC=CC=1>FC(F)(F)C(O)=O>[ClH:1].[NH:37]([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C:30](=[O:41])[NH:29][CH:11]([OH:10])[C:12](=[O:28])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:38]([NH2:40])=[NH:39]

Participants

3

Reactant 1

HCID 178451103HCID 178451103, compound

Product 1

HCID 178479433HCID 178479433, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.95 g (1.53 mmol) of t-butyl 11-benzyloxy-19-guanidino-10,13-dioxo-4,9,12-triazanonadecanoate dihydrochloride was dissolved in 10 ml of trifluoroacetic acid under ice-cooling and then allowed to react at room temperature overnight. The trifluoroacetic acid was distilled off under reduced pressure and the residue was dissolved in 10 ml of distilled water. After washing with 1,2-dichloroethane, the pH value of the product was adjusted to 5.0 with 1N NaOH. Then it was diluted to approximately 2 l with distilled water, adsorbed on 125 ml of CM-Sephadex® C-25 (Na) and subjected to gradient elution between 1 l of distilled water and 1 l of 0.07M sodium chloride. The target fractions were combined and concentrated to dryness. The insoluble matters were filter off using 90% ethanol and the filtrate was further desalted with 100 ml of Diaion® HP-20. By eluting with distilled water and lyophilizing, 149.5 mg of the aimed compound was obtained (yield: 22.3%).

Workup

  1. temperaturecooling
  2. customto react at room temperature overnight
  3. distillationThe trifluoroacetic acid was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in 10 ml of distilled water
  5. washAfter washing with 1,2-dichloroethane
  6. additionThen it was diluted to approximately 2 l with distilled water
  7. wash(Na) and subjected to gradient elution between 1 l of distilled water and 1 l of 0.07M sodium chloride
  8. concentrationconcentrated to dryness
  9. filtrationThe insoluble matters were filter off
  10. washBy eluting with distilled water

Sources & evidence

ORD record
ord-c68b870b1c804e48acd50c927bdf101f
Source dataset
uspto-grants-1991_02
Patent number
US04990536

Reaction notes

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