Hydrochloric Acid → (E)-4-(2-(4-((2,4-Dioxothiazolidin-5-ylidene)methyl)phenoxy)ethoxy)benzoic acid

HRID 852965Notes

Reaction equation

[O:1]=[C:2]1[NH:6][C:5](=[O:7])/[C:4](=[CH:8]\[C:9]2[CH:28]=[CH:27][C:12]([O:13][CH2:14][CH2:15][O:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)/[S:3]1.CO.O.[OH-].[Li+].Cl>C1COCC1.O>[O:1]=[C:2]1[NH:6][C:5](=[O:7])/[C:4](=[CH:8]\[C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)=[CH:27][CH:28]=2)/[S:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl ester 356 (647 mg, 1.62 mmol) in THF (15 mL) was added methanol (2 mL), water (2 mL) and lithium hydroxide monohydrate (340 mg, 8.11 mmol). The mixture was heated at 60° C. for 1 hour, acidified with 10% HCl solution and extracted with ethyl acetate. The organic extract was dried over MgSO4, filtered, and evaporated to afford the title compound (141 mg, 22%). 1H NMR: (MeOD-d4) δ (ppm): 7.97 (d, J=8.8 Hz, 2H), 7.75 (s, 1H), 7.53 (d, J=8.8 Hz, 2H), 7.12 (d, J=8.8 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 4.44 (4H, bs). LRMS (ESI): (calc.) 385.4; (found) 392.3 (MLi)+.

Workup

extractionextracted with ethyl acetate
extractionThe organic extract
dry with materialwas dried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-13acbc105ec44f5bb89db49186386e38
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253204B2

Reaction notes

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