Lithium Hydroxide → HCID 59381875, compound

HRID 2355090Notes

Reaction equation

HRID 2355090 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]([CH3:25])=[C:19]([CH:24]=1)[C:20]([O:22]C)=[O:21])=[O:14].C1COCC1.[OH-].[Li+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]([CH3:25])=[C:19]([CH:24]=1)[C:20]([OH:22])=[O:21])=[O:14]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59381898HCID 59381898, compound

Product 1

HCID 59381875HCID 59381875, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 5-((2-fluoro-5-(trifluoromethyl)phenyl)carbamoyl)-2-methylbenzoate 35 (0.904 g, 2.5 mmol), THF (20 mL), lithium hydroxide (0.18 g, 7.6 mmol), and water (5 mL) was heated at 55° C. for 24 hours and then cooled to room temperature. The aqueous layer was separated, cooled in an ice-water bath, and acidified with 6 M HCl (aq) to pH 1. This solution was extracted with ethyl acetate (3×10 mL), and the combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated to afford 5-((2-fluoro-5-(trifluoromethyl)phenyl)carbamoyl)-2-methylbenzoic acid 36.

Workup

  1. customThe aqueous layer was separated
  2. temperaturecooled in an ice-water bath
  3. extractionThis solution was extracted with ethyl acetate (3×10 mL)
  4. dry with materialthe combined organic phases were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7fa4f376f076441eab07f3fff41b23ef
Source dataset
uspto-grants-2010_07
Patent number
US07754717B2

Reaction notes

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