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

HRID 602984Notes

Reaction equation

HRID 602984 reaction equation
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]2[CH2:11][CH:10]([CH:12]([C:17]3[CH:18]=C([CH:22]=[C:23]([F:25])[CH:24]=3)C#N)[C:13]([F:16])([CH3:15])[CH3:14])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:32].[Na+].Cl.[CH3:35][CH2:36][OH:37]>>[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]2[CH2:11][CH:10]([CH:12]([C:17]3[CH:18]=[C:35]([CH:22]=[C:23]([F:25])[CH:24]=3)[C:36]([OH:32])=[O:37])[C:13]([F:16])([CH3:15])[CH3:14])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 113390333-{1-[(Diphenylmethyl)azetidin-3-yl]-2-fluoro-2-methylpropyl}-5-fluorobenzonitrile

Product 1

HCID 670553813-{1-[1-(Diphenylmethyl)azetidin-3-yl]-2-fluoro-2-methylpropyl}-5-fluorobenzoic acid

Procedure

The reaction of mixture of 7.15 g (17.18 mmol) of 3-{1-[1(diphenylmethyl)azetidin-3-yl]-2-fluoro-2-methylpropyl}-5-fluorobenzonitrile (Step 1), 125 mL of EtOH, and 70 mL of 5N NaOH was refluxed for 3.5 h. Then it was adjusted to pH=4-5 with 12N HCl and concentrated to remove solvents. To the residue was added 200 mL of CH2Cl2 to dissolve the compound and it was filtered to remove the solid. The solid layer was washed with CH2Cl2 and the combined organic layers were concentrated to afford the title compound as white solid; Mass Spectrum: m/e=436 (M+1).

Workup

  1. temperaturewas refluxed for 3.5 h
  2. concentrationconcentrated
  3. customto remove solvents
  4. additionTo the residue was added 200 mL of CH2Cl2
  5. dissolutionto dissolve the compound and it
  6. filtrationwas filtered
  7. customto remove the solid
  8. washThe solid layer was washed with CH2Cl2
  9. concentrationthe combined organic layers were concentrated

Sources & evidence

ORD record
ord-1a04aa1fea0544c0ab9cf9be6b249eae
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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