Trifluoroacetic acid → HCID 22122234, compound

HRID 1859167Notes

Reaction equation

HRID 1859167 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 trifluoroacetate. 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-butoxycarbonylamidinophenoxy)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-d20ff642047846fbacf8818b29aefe36
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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