Hydrochloric Acid → 5-[(Dimethylamino)sulfonyl]-2-[(phenylmethyl)oxy]benzoic acid

HRID 1623685Notes

Reaction equation

[Li+].[OH-].[CH3:3][N:4]([CH3:26])[S:5]([C:8]1[CH:9]=[CH:10][C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([CH:17]=1)[C:13]([O:15]C)=[O:14])(=[O:7])=[O:6].Cl>O1CCCC1.O.C(OCC)(=O)C>[CH3:3][N:4]([CH3:26])[S:5]([C:8]1[CH:9]=[CH:10][C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([CH:17]=1)[C:13]([OH:15])=[O:14])(=[O:6])=[O:7]

Participants

Conditions

Temperature: 50 °C

Procedure

LiOH (20.56 mg, 0.86 mmol) was added to a stirred solution of methyl 5-[(dimethylamino) sulfonyl]-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 62; 300 mg, 0.86 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. 230 mg.

Workup

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

Sources & evidence

ORD record: ord-690fd63f38ad4154860cb724faf0cfeb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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