Hydrochloric Acid → 3-(1-{1-[(4-Chlorophenyl)(3-cyanophenyl)methyl]azetidin-3-yl}-2-fluoro-2-methylpropyl)-5-fluorobenzoic acid

HRID 602991Notes

Reaction equation

HRID 602991 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[N:37])[CH:31]=2)[N:9]2[CH2:12][CH:11]([CH:13]([C:18]3[CH:19]=[C:20]([CH:26]=[C:27]([F:29])[CH:28]=3)[C:21]([O:23]CC)=[O:22])[C:14]([F:17])([CH3:16])[CH3:15])[CH2:10]2)=[CH:4][CH:3]=1.[Li+].[OH-].Cl>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[N:37])[CH:31]=2)[N:9]2[CH2:12][CH:11]([CH:13]([C:18]3[CH:19]=[C:20]([CH:26]=[C:27]([F:29])[CH:28]=3)[C:21]([OH:23])=[O:22])[C:14]([F:17])([CH3:16])[CH3:15])[CH2:10]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67055325HCID 67055325, compound

Product 1

HCID 670553863-(1-{1-[(4-Chlorophenyl)(3-cyanophenyl)methyl]azetidin-3-yl}-2-fluoro-2-methylpropyl)-5-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 112 mg (0.214 mmol) of ethyl 3-(1-{1-[(4-chlorophenyl)(3-cyanophenyl)methyl]azetidin-3-yl}-2-fluoro-2-methylpropyl)-5-fluorobenzoate and 1.2 mL of 1M LiOH in 5 mL of EtOH was stirred for 2.5 h at rt. The solution was adjusted to pH=5-6 with 6N HCl and concentrated to remove solvents. The residue was dissolve in 10 mL of CH2Cl2 and solids were removed by filtration. The solution was concentrated to afford the title compound as a white solid; Mass Spectrum: m/e=495 (M+1, 35Cl), 497 (M+1, 37Cl).

Workup

  1. concentrationconcentrated
  2. customto remove solvents
  3. dissolutionThe residue was dissolve in 10 mL of CH2Cl2
  4. customsolids were removed by filtration
  5. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-034f6d11a58b44c0ab27c4f78b25ebd7
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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