Trifluoroacetic acid → HCID 9846037, compound

HRID 1859189Notes

Reaction equation

HRID 1859189 reaction equation
C(OC([NH:8][C:9]([C:11]1[CH:52]=[CH:51][C:14]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([CH:25]([C:43]3[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=3)[CH2:26][C:27]([O:29]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:28])[C:21](=[O:49])[C:20]2=[O:50])=[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]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([CH:25]([C:43]3[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=3)[CH2:26][C:27]([OH:29])=[O:28])[C:21](=[O:49])[C:20]2=[O:50])=[CH:51][CH:52]=1)(=[NH:8])[NH2:10]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 140397795HCID 140397795, compound

Product 1

HCID 9846037HCID 9846037, compoundYield 57.3%

Procedure

A mixture of 2.3 g of diphenylmethyl 3-[4-[3-(4-tert-butoxycarbonylamidinophenoxy)propyl]-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)propionate, 18.5 ml of anisole and 37 ml of trifluoroacetic acid was stirred at room temperature for 3 hours and then distilled under reduced pressure to remove the solvent. The resulting residue was suspended in a mixed solvent of 15 ml of ethyl acetate and 13 ml of water, followed by adding thereto 0.55 g of sodium hydrogencarbonate, and the resulting mixture was stirred at room temperature for 30 minutes. The aqueous layer was separated, adjusted to pH 3.5 with a saturated aqueous sodium hydrogencarbonate solution, and then concentrated to a volume of about 10 ml under reduced pressure. The resulting concentrate was purified by a reversed phase column chromatography (eluent: 25% aqueous acetonitrile solution) to obtain 0.82 g of 3-[4-[3-(4-amidinophenoxy)propyl]-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)propionic acid as colorless crystals.

Workup

  1. distillationdistilled under reduced pressure
  2. customto remove the solvent
  3. additionby adding
  4. stirring0.55 g of sodium hydrogencarbonate, and the resulting mixture was stirred at room temperature for 30 minutes
  5. customThe aqueous layer was separated
  6. concentrationconcentrated to a volume of about 10 ml under reduced pressure
  7. concentrationThe resulting concentrate
  8. customwas purified by a reversed phase column chromatography (eluent: 25% aqueous acetonitrile solution)

Sources & evidence

ORD record
ord-a1351856bbe94288bed4e477c3a6ee38
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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