Hydrochloric Acid → (3-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2-oxo-2,3-dihydro-benzooxazol-6-yloxy)-acetic acid

HRID 1710648Notes

Reaction equation

HRID 1710648 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][O:6][C:7]1[CH:34]=[CH:33][C:10]2[N:11]([CH2:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([O:31][CH3:32])[CH:25]=4)[CH2:20][CH2:19]3)=[O:17])[C:12](=[O:14])[O:13][C:9]=2[CH:8]=1)C.Cl>C1COCC1.[OH-].[Na+]>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([N:21]2[CH2:20][CH2:19][N:18]([C:16](=[O:17])[CH2:15][N:11]3[C:10]4[CH:33]=[CH:34][C:7]([O:6][CH2:5][C:4]([OH:35])=[O:3])=[CH:8][C:9]=4[O:13][C:12]3=[O:14])[CH2:23][CH2:22]2)=[CH:25][C:26]=1[O:31][CH3:32]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58834369(3-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2-oxo-2,3-dihydro-benzooxazol-6-yloxy)-acetic acid ethyl ester

Product 1

HCID 16059629(3-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2-oxo-2,3-dihydro-benzooxazol-6-yloxy)-acetic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of (3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2-oxo-2,3-dihydro-benzooxazol-6-yloxy)-acetic acid ethyl ester (45) in THF (3 ml) and NaOH (2N, 3 ml) was stirred at rt for 2 hours. The reaction mixture was neutralized with HCl (1 N), extracted with ethyl acetate, washed with water, and purified by flash chromatography to provide (3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2-oxo-2,3-dihydro-benzooxazol-6-yloxy)-acetic acid (46): LCMS observed for (M+H)+: 476.5

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c3642dfacab0444b80967cbfaf788b7b
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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