Hydrochloric Acid → 5-[(4-Methyl-1-piperazinyl)sulfonyl]-2-[(phenylmethyl)oxy]benzoic acid

HRID 1623694Notes

Reaction equation

[Li+].[OH-].[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[CH:14]=[CH:15][C:16]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:17]([CH:22]=2)[C:18]([O:20]C)=[O:19])(=[O:12])=[O:11])[CH2:6][CH2:5]1.Cl>O1CCCC1.O.C(OCC)(=O)C>[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[CH:14]=[CH:15][C:16]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:17]([CH:22]=2)[C:18]([OH:20])=[O:19])(=[O:12])=[O:11])[CH2:6][CH2:5]1

Participants

Conditions

Temperature: 50 °C

Procedure

LiOH (15.39 mg, 0.64 mmol) was added to a stirred solution of methyl 5-[(4-methyl-1-piperazinyl) sulfonyl]-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 71; 260 mg, 0.64 mmol) in a mixture of tetrahydrofuran and water (3:1, 40 ml). The mixture was heated at 50° C. for 6 h and then diluted with ethyl acetate (50 nil). 10% Aqueous HCl was added to the mixture to adjust pH to 2. The organic phase was isolated, washed with brine, dried over MgSO4, and concentrated to yield the title compound as a white solid. 120 mg.

Workup

customThe organic phase was isolated
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-9f4cd88d4e0045d495e1a61ab6a4e668
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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