Water → 1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid

HRID 476364Notes

Reaction equation

HRID 476364 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]([O:16]C)=[O:15])[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.O.O.[OH-].[Li+]>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]2)=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66598761METHYL 1-[(4-FLUOROPHENYL)CARBAMOYL]CYCLOPROPANECARBOXYLATE

Product 1

HCID 210815301-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic AcidYield 94.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylate (3.28 g, 14.00 mmol) was dissolved in THF (23.34 mL), water (11.67 mL) was added, followed by lithium hydroxide monohydrate (1.763 g, 42.0 mmol), and the mixture stirred at room temperature for 30 minutes. After this time the THF was removed under reduced pressure and the pH of the water layer was adjusted to ˜5 with 2 M HCl while the solution was cooled in an ice bath. The precipitate that formed was dissolved in ethyl acetate (125 mL) and the layers were separated. The organic layer was washed with water (100 mL) and brine (100 mL) and then dried over magnesium sulfate. Evaporation of the solvent yielded 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (2.952 g, 94% yield) as an off white powder. 1H NMR (400 MHz, DMSO-d6): δ 13.06 (broad s, 1H), 10.56 (s, 1H), 7.60 (m, 2H), 7.12 (m, 2H), 1.39 (s, 4H); MS (ESI) m/z: 224.1 (M+H+).

Workup

  1. customAfter this time the THF was removed under reduced pressure
  2. temperaturewas cooled in an ice bath
  3. customThe precipitate that formed
  4. customthe layers were separated
  5. washThe organic layer was washed with water (100 mL) and brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3f59b4ba9a634e24a75c342b153d4fae
Source dataset
uspto-grants-2014_01
Patent number
US08637672B2

Reaction notes

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