Hydrochloric Acid → HCID 67055384, compound

HRID 603011Notes

Reaction equation

HRID 603011 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH:14]2[CH2:17][N:16]([C@@H:18]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[C:19]3[CH:20]=C([CH:24]=[CH:25][CH:26]=3)C#N)[CH2:15]2)[C:10]([F:13])([CH3:12])[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[OH-:34].[Na+].Cl.[CH3:37][CH2:38][OH:39]>>[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH:14]2[CH2:17][N:16]([C@@H:18]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[C:19]3[CH:20]=[C:37]([CH:24]=[CH:25][CH:26]=3)[C:38]([OH:34])=[O:39])[CH2:15]2)[C:10]([F:13])([CH3:12])[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 67055313HCID 67055313, compound

Product 1

HCID 67055384HCID 67055384, compound

Procedure

A mixture of 5.52 g (10.4 mmol) of 3-[(S)-{3-[(1S)-1-(3-bromo-5-fluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl}(4-chlorophenyl)methyl]benzonitrile, 65 mL of EtOH, and 40 mL of 5N NaOH was heated to reflux for 4 h (with monitoring by HPLC). Then the pH solution was adjusted to 4-5 with 12N HCl and the solution was concentrated to remove organic solvents. The residue was dissolved in 200 mL of CH2Cl2 and filtered to remove undissolved solid. The solid residue was triturated with two 200 mL portions of CH2Cl2 and the combined organic layers were concentrated to the title compound as white solid; Mass Spectrum: m/e=548, (M+1, 35Cl 79Br), 550 (M+1, 37Cl79Br/35Cl 81Br), 552 (M+1, 37Cl 81Br).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h (with monitoring by HPLC)
  3. concentrationthe solution was concentrated
  4. customto remove organic solvents
  5. dissolutionThe residue was dissolved in 200 mL of CH2Cl2
  6. filtrationfiltered
  7. customto remove undissolved solid
  8. customThe solid residue was triturated with two 200 mL portions of CH2Cl2
  9. concentrationthe combined organic layers were concentrated to the title compound as white solid

Sources & evidence

ORD record
ord-6bb85b8127e6423cbd6ef15165443b97
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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