Lithium Hydroxide → 4-((1-Benzoylazetidin-3-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid

HRID 1849892Notes

Reaction equation

HRID 1849892 reaction equation
[C:1]([N:9]1[CH2:12][CH:11]([CH2:13][O:14][C:15]2[C:24]([CH:25]3[CH2:27][CH2:26]3)=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[C:17]([F:28])[CH:16]=2)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[C:1]([N:9]1[CH2:10][CH:11]([CH2:13][O:14][C:15]2[C:24]([CH:25]3[CH2:26][CH2:27]3)=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[C:17]([F:28])[CH:16]=2)[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86703770HCID 86703770, compound

Product 1

HCID 867037714-((1-Benzoylazetidin-3-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidYield 75.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-((1-benzoylazetidin-3-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate (70 mg, 0.18 mmol) and lithium hydroxide (22 mg, 0.91 mmol) in THF (5 mL) and H2O (10 ml) was stirred at room temperature for 18 h. The mixture was quenched with HCl (1N, 2 mL) and extracted with ethyl acetate (10 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to get the target compound (50 mg, 74%) as a yellow solid. LCMS (ESI) m/z: 370.1 [M+H].

Workup

  1. customThe mixture was quenched with HCl (1N, 2 mL)
  2. extractionextracted with ethyl acetate (10 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-615ae1f9867e499e8e141b7179d9f99f
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…