Hydrochloric Acid → 5-(4-Morpholinylsulfonyl)-2-[(phenylmethyl)oxy]benzoic acid

HRID 1623688Notes

Reaction equation

[Li+].[OH-].[N:3]1([S:9]([C:12]2[CH:13]=[CH:14][C:15]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:16]([CH:21]=2)[C:17]([O:19]C)=[O:18])(=[O:11])=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.Cl>O1CCCC1.O.C(OCC)(=O)C>[N:3]1([S:9]([C:12]2[CH:13]=[CH:14][C:15]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[C:16]([CH:21]=2)[C:17]([OH:19])=[O:18])(=[O:11])=[O:10])[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1

Participants

Conditions

Temperature: 50 °C

Procedure

LiOH (23.25 mg, 0.97 mmol) was added to a stirred solution of methyl 5-(4-morpholinylsulfonyl)-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 65; 380 mg, 0.97 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 m). 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. 250 mg.

Workup

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

Sources & evidence

ORD record: ord-4b946224fe7046718b9563667b46a463
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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