Hydrochloric Acid → 2-[(Phenylmethyl)oxy]-5-(1-piperidinylsulfonyl)benzoic acid

HRID 1623691Notes

Reaction equation

[Li+].[OH-].[C:3]1([CH2:9][O:10][C:11]2[CH:20]=[CH:19][C:18]([S:21]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)(=[O:23])=[O:22])=[CH:17][C:12]=2[C:13]([O:15]C)=[O:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>O1CCCC1.O.C(OCC)(=O)C>[C:3]1([CH2:9][O:10][C:11]2[CH:20]=[CH:19][C:18]([S:21]([N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)(=[O:23])=[O:22])=[CH:17][C:12]=2[C:13]([OH:15])=[O:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

LiOH (20.29 mg, 0.847 mmol) was added to a stirred solution of methyl 2-[(phenylmethyl)oxy]-5-(1-piperidinylsulfonyl)benzoate (may be prepared as described in Description 68; 330 mg, 0.85 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 ml). 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. 220 mg.

Workup

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

Sources & evidence

ORD record: ord-6863559b5fd24c1a933c02eaf3c10166
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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