Hydrochloric Acid → HCID 69656069, compound

HRID 11684Notes

Reaction equation

HRID 11684 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][CH2:6][C:7]1[C:8]([O:14][CH2:15][C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:20][C@H:19]2[CH3:33])=[O:17])=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1)C.O.[OH-].[Li+].Cl.P([O-])([O-])([O-])=O>O1CCCC1.CO.O>[Cl:13][C:11]1[CH:12]=[C:7]([CH2:6][CH2:5][C:4]([OH:34])=[O:3])[C:8]([O:14][CH2:15][C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:20][C@H:19]2[CH3:33])=[O:17])=[N:9][CH:10]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 168937Lithium hydroxide, monohydrateHCID 69655855HCID 69655855, compound

Product 1

HCID 69656069HCID 69656069, compoundYield 25.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-propionic acid ethyl ester (0.081 g, 0.17 mmol) in tetrahydrofuran (2 mL), methanol (2 mL) and water (1 mL) was added lithium hydroxide monohydrate (0.013 g, 0.32 mmol). The reaction mixture was stirred at ambient temperature for 3 hours, neutralized with 0.2M hydrochloric acid and phosphate buffer (pH=7), and extracted with ethy acetate. The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Purification with via HPLC gave the title compound (0.020 g, LRMS: 464.4).

Workup

  1. extractionextracted with ethy acetate
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification with via HPLC

Sources & evidence

ORD record
ord-68e99a9f7abe4ad6afcd22c1448cb0c6
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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