Lithium Hydroxide → HCID 86703763, compound

HRID 1849877Notes

Reaction equation

HRID 1849877 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:9]2[CH2:12][CH:11]([CH2:13][O:14][C:15]3[C:24]([CH:25]4[CH2:27][CH2:26]4)=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[C:17]([F:28])[CH:16]=3)[CH2:10]2)=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:9]2[CH2:12][CH:11]([CH2:13][O:14][C:15]3[C:24]([CH:25]4[CH2:27][CH2:26]4)=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[C:17]([F:28])[CH:16]=3)[CH2:10]2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86703761Methyl 4-((1-((4-chlorophenyl)(phenyl)-methyl)azetidin-3-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate

Product 1

HCID 86703763HCID 86703763, compoundYield 107.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 4-((1-((4-chlorophenyl)(phenyl)methyl)azetidin 3-yl)-methoxy)-5-cyclopropyl-2-fluorobenzoate (50 mg, 0.10 mmol) and lithium hydroxide (13 mg, 0.31 mmol) in THF (10 mL) and H2O (10 mL) was stirred at 50° C. for 3 h. The mixture was diluted with EtOAc (100 mL), washed with HCl (2.0 M, 20 mL), brine (50×2 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the target product (50 mg) as oil which was used in the next step without further purification. LCMS (ESI) m/z: 466.1 [M+H]+.

Workup

  1. washwashed with HCl (2.0 M, 20 mL), brine (50×2 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5799914d0fdf4fd69f4c1ce240f7d8d5
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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