Hydrochloric Acid → 3-[4-(2-Bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid

HRID 1665655Notes

Reaction equation

HRID 1665655 reaction equation
C([O:5][C:6](=[O:25])[CH2:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Br:23])[CH2:12][CH2:11]1)=[O:9])(C)(C)C.Cl>O1CCOCC1>[Br:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([N:13]1[CH2:14][CH2:15][N:10]([C:8](=[O:9])[CH2:7][C:6]([OH:25])=[O:5])[CH2:11][CH2:12]1)=[O:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 578757933-[4-(2-Bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid tert-butyl ester

Product 1

HCID 578758013-[4-(2-Bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acidYield 87.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid tert-butyl ester (400 mg, 0.97 mmol) in dioxane.HCl (4 mL) was stirred at 0° C. for 30 minutes. The reaction mixture was concentrated to afford 300 mg of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid. LCMS: 356.02 (M+1)+, 96.9%, H1NMR: (DMSO-d6): δ 12.6 (s, 1H), 7.7 (d, 1H), 7.54-7.32 (m, 3H), 3.7-3.4 (m, 8H), 3.2-3.06 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-787ad03e29a143fcaa28c2f3c91f61ff
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

Loading…