Trifluoroacetic acid → HCID 22122219, compound

HRID 1859191Notes

Reaction equation

HRID 1859191 reaction equation
C(OC([NH:8][C:9]([C:11]1[CH:53]=[CH:52][C:14]([C:15]([NH:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][N:23]([CH:26]([C:44]3[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=3)[CH2:27][C:28]([O:30]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:29])[C:22](=[O:50])[C:21]2=[O:51])=[O:16])=[CH:13][CH:12]=1)=[NH:10])=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[C:9]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([NH:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][N:23]([CH:26]([C:44]3[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=3)[CH2:27][C:28]([OH:30])=[O:29])[C:22](=[O:50])[C:21]2=[O:51])=[O:16])=[CH:52][CH:53]=1)(=[NH:8])[NH2:10]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 140397801HCID 140397801, compound

Product 1

HCID 22122219HCID 22122219, compoundYield 31.8%

Procedure

To a mixture of 0.1 g of diphenylmethyl 3-[4-[2-(4-tert-butoxycarbonylamidinobenzoyl)aminoethyl]-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)propionate and 1 ml of anisole was added 2 ml of trifluoroacetic acid, and the resulting mixture was stirred at room temperature for 3 hours. Then, the solvent was distilled off under reduced pressure and 2 ml of ethyl acetate, 1 ml of water and 1 ml of acetonitrile were added to the residue. To the resulting mixture was added 0.023 g of sodium hydrogencarbonate, followed by stirring at room temperature for 10 minutes. Thereafter, the aqueous layer was separated and then concentrated to a volume of about 0.5 ml under reduced pressure. The resulting concentrate was purified by a reversed phase column chromatography (eluent: a 10% aqueous acetonitrile solution) to obtain 0.02 g of 3-[4-[2-(4-amidinobenzoyl)aminoethyl]-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)propionic acid as colorless crystals.

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure and 2 ml of ethyl acetate, 1 ml of water and 1 ml of acetonitrile
  2. additionwere added to the residue
  3. additionTo the resulting mixture was added 0.023 g of sodium hydrogencarbonate
  4. stirringby stirring at room temperature for 10 minutes
  5. customThereafter, the aqueous layer was separated
  6. concentrationconcentrated to a volume of about 0.5 ml under reduced pressure
  7. concentrationThe resulting concentrate
  8. customwas purified by a reversed phase column chromatography (eluent

Sources & evidence

ORD record
ord-472461886d814af0b29b4948e107785c
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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