Hydrochloric Acid → (S)-1-(4-Chloro-3,5-dimethyl-phenyl)-2,2,2-trifluoro-ethylamine

HRID 1629737Notes

Reaction equation

HRID 1629737 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]([NH:14][S@@](C(C)(C)C)=O)[C:10]([F:13])([F:12])[F:11])=[CH:4][C:3]=1[CH3:21].Cl>CO>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]([NH2:14])[C:10]([F:12])([F:13])[F:11])=[CH:4][C:3]=1[CH3:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67345793(R)-2-Methyl-propane-2-sulfinic acid [(S)-1-(4-chloro-3,5-dimethyl-phenyl)-2,2,2-trifluoro-ethyl]-amide

Product 1

HCID 57517336(S)-1-(4-Chloro-3,5-dimethyl-phenyl)-2,2,2-trifluoro-ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of intermediate INT 42 (860 mg, 2.52 mmol) in MeOH (40 mL) was treated with HCl (4 M in dioxane, 1.26 mL, 5.04 mmol) and stirred over the weekend. After evaporation of the solvents, a solid was obtained which was triturated with Et2O. The solid was then dissolved in water and the pH was adjusted to ˜9 using 10% sodium carbonate solution. It was extracted twice with EtOAc. The combined extracts were dried over sodium sulfate, filtered and concentrated.

Workup

  1. customAfter evaporation of the solvents
  2. customa solid was obtained which
  3. customwas triturated with Et2O
  4. dissolutionThe solid was then dissolved in water
  5. extractionIt was extracted twice with EtOAc
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b42165ca4eed4775a06c06d6dc78420c
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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