Trifluoroacetic acid → HCID 22122234, compound

HRID 1417207Notes

Reaction equation

HRID 1417207 reaction equation
C(OC([NH:11][C:12]([C:14]1[CH:42]=[CH:41][C:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25](CC3C=CC(OC)=CC=3OC)[C:24](=[O:39])[C:23]2=[O:40])=[CH:16][CH:15]=1)=[NH:13])=O)C1C=CC=CC=1.[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46]>C1(OC)C=CC=CC=1>[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[C:12]([C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][NH:25][C:24](=[O:39])[C:23]2=[O:40])=[CH:41][CH:42]=1)(=[NH:11])[NH2:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 140412946HCID 140412946, compound

Product 1

HCID 22122234HCID 22122234, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

In 16.5 ml of anisole was dissolved 8.25 g of 4-[3-(4-benzyloxycarbonylamidinophenoxy)propyl]-1-(2,4-dimethoxybenzyl)-2,3-dioxopiperazine, and 33 ml of trifluoroacetic acid was added to the solution, followed by refluxing for 5 hours. After cooling, the solvent was distilled off under reduced pressure. To the resulting residue was added 40 ml of ethyl acetate, and stirred for 30 minutes, after which the precipitate was collected by filtration and dried to obtain 8.23 g of 4-[3-(4-amidinophenoxy)propyl]-2,3-dioxopiperazine trifluoro-acetate. Then, the compound obtained was dissolved in a mixed solvent of 182 ml of dioxane and 82 ml of water, followed by adding thereto 8.37 g of sodium carbonate and 3.62 g of di-tert-butyl dicarbonate, and the resulting mixture was stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 80 ml of ethyl acetate and 80 ml of water were added to the resulting residue and stirred for 30 minutes. The crystals precipitated were collected by filtration and dried to obtain 4.27 g of 1-[3-(4-tert-butoxycarbonyl-amidinophenoxy)propyl]-2,3-dioxopiperazine as colorless crystals.

Workup

  1. additionwas added to the solution
  2. temperatureby refluxing for 5 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the resulting residue was added 40 ml of ethyl acetate
  6. filtrationafter which the precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-db5d691a8c11499ca1d6e2a33d2868cd
Source dataset
uspto-grants-1999_03
Patent number
US05877174

Reaction notes

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