Lithium Hydroxide → 4-[2-Anilino-1-(anilinocarbonyl)-1-hydroxy-2-oxoethyl]benzoic acid

HRID 1694836Notes

Reaction equation

[NH:1]([C:8](=[O:28])[CH:9]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-:30]>C1COCC1.O.C(OCC)(=O)C>[NH:1]([C:8](=[O:28])[C:9]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][CH:27]=1)([C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[OH:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid in THF (5 mL) at room temperature was added a solution of LiOH (28 mg, 1.2 mmol) in water (2 mL). The reaction mixture was stirred open to air for 20 h then heated to 40° C. for 8 h. Additional LiOH (20 mg, 0.83 mmol) was added and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with ethyl acetate, washed with 1 M HCl (1×), brine (1×), dried over MgSO4, and concentrated. Purification by reverse phase HPLC (30% to 100% MeCN in water) gave 4-[2-anilino-1-(anilinocarbonyl)-1-hydroxy-2-oxoethyl]benzoic acid (31 mg, 25%) as a white solid: ESIMS calcd 391.1 (M++H), found 391.1 (M++H).

Workup

stirringthe reaction mixture was stirred at room temperature for 18 h
washwashed with 1 M HCl (1×), brine (1×)
dry with materialdried over MgSO4
concentrationconcentrated
customPurification by reverse phase HPLC (30% to 100% MeCN in water)

Sources & evidence

ORD record: ord-8b1880fc92b54123af6f12e3b992afb4
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158825B2

Reaction notes

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