Hydrochloric Acid → 4-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-butyric Acid

HRID 11719Notes

Reaction equation

HRID 11719 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:10]([O:16][CH2:17][C:18]([N:20]2[CH2:25][C@H:24]([CH3:26])[N:23]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH2:22][C@H:21]2[CH3:35])=[O:19])=[N:11][CH:12]=[C:13]([Cl:15])[CH:14]=1)C.CO.O.[OH-].[Li+].Cl>[Cl-].[Na+].O.O.O1CCCC1>[Cl:15][C:13]1[CH:14]=[C:9]([NH:8][CH2:7][CH2:6][CH2:5][C:4]([OH:36])=[O:3])[C:10]([O:16][CH2:17][C:18]([N:20]2[CH2:25][C@H:24]([CH3:26])[N:23]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH2:22][C@H:21]2[CH3:35])=[O:19])=[N:11][CH:12]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 696559714-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-butyric acid ethyl ester

Product 1

HCID 696554194-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-butyric Acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-butyric acid ethyl ester (0.034 g, 0.065 mmol) in 2:2:1 methanol:tetrahydrofuran:water (1 mL) was added lithium hydroxide monohydrate (0.010 g, 0.24 mmol). The reaction was stirred at ambient temperature for 3 hours. The pH of the solution was adjusted to ˜4 by the addition of 0.2 M hydrochloric acid, then diluted with brine and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The product was purified by anion exchange chromatography to give the title compound as its acetic acid addition salt (0.020 g, LRMS: 493.1, 495.3)

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by anion exchange chromatography

Sources & evidence

ORD record
ord-ae37d774b45846459eb1e9a505a95ad7
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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