Lithium hydroxide, monohydrate → HCID 71208481, compound

HRID 1887912Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:32])[C:7]([CH2:18][NH:19][C:20]([C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=3)=[O:21])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:32])[C:7]([CH2:18][NH:19][C:20]([C:22]3[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=3)=[O:21])=[CH:8][N:9]2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of methyl 4-((7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methylcarbamoyl)benzoate (128 mg, 0.286 mmol) in tetrahydrofuran (2.3 mL) at 25° C. was treated with a solution of lithium hydroxide monohydrate (24.0 mg, 0.573 mmol) in water (573 μL). The reaction was stirred at 25° C. for 24 hr. At this time, LC/MS indicated complete conversion to the desired acid. The reaction was diluted with water (30 mL) and was extracted with methylene chloride (1×50 mL). The aqueous layer was then acidified with a 1N aqueous hydrochloric acid solution, and then extracted with 90:10 methylene chloride-methanol (3×40 mL). The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo to give the intermediate 4-((7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methylcarbamoyl)benzoic acid (55.1 mg, 44%).

Workup

extractionwas extracted with methylene chloride (1×50 mL)
extractionextracted with 90:10 methylene chloride-methanol (3×40 mL)
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-21c64743ed7c4386a8689239c6c4c4e1
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Reaction notes

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