Hydrochloric Acid → HCID 22122220, compound

HRID 1859190Notes

Reaction equation

HRID 1859190 reaction equation
C(OC([NH:8][C:9]([C:11]1[CH:41]=[CH:40][C:14]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([CH:25]([C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:21](=[O:38])[C:20]2=[O:39])=[CH:13][CH:12]=1)=[NH:10])=O)(C)(C)C.[ClH:42]>C(OCC)(=O)C.O1CCOCC1>[ClH:42].[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:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:21](=[O:38])[C:20]2=[O:39])=[CH:40][CH:41]=1)(=[NH:8])[NH2:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 140397800HCID 140397800, compound

Product 1

HCID 22122220HCID 22122220, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

In 2 ml of ethyl acetate was dissolved 0.45 g of ethyl 3-[4-[3-(4-tert-butoxycarbonylamidinophenoxy)-propyl]-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)-propionate, followed by adding thereto 4 ml of a 2.4N solution of hydrochloric acid in dioxane, and the resulting mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the resulting residue was purified by a reversed phase column chromatography (eluent: a 15% aqueous acetonitrile solution) to obtain 0.20 g of ethyl 3-[4-[3-(4-amidinophenoxy)propyl]-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)propionate hydrochloride as a white solid.

Workup

  1. additionby adding
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified by a reversed phase column chromatography (eluent

Sources & evidence

ORD record
ord-4394223e1bb44029876957dfa4aded38
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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