Hydrochloric Acid → 5-[(S)-1-(4-Chloro-3-methyl-phenyl)-2,2,2-trifluoro-ethylamino]-2-methyl-benzaldehyde

HRID 1629725Notes

Reaction equation

HRID 1629725 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([CH:21]3OCC[O:22]3)[CH:15]=2)[C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[CH3:26].Cl>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([CH:15]=2)[CH:21]=[O:22])[C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[CH3:26]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68258686[(S)-1-(4-Chloro-3-methyl-phenyl)-2,2,2-trifluoro-ethyl]-(3-[1,3]dioxolan-2-yl-4-methyl-phenyl)-amine

Product 1

HCID 866562265-[(S)-1-(4-Chloro-3-methyl-phenyl)-2,2,2-trifluoro-ethylamino]-2-methyl-benzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of acetal INT 32 (4.91 g, 12.73 mmol) in THF (127 mL) at 0° C. was added HCl (2 M in H2O, 25.5 mL, 50.92 mmol). The reaction mixture was stirred at room temperature for 100 minutes. The mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3 (2×), water (2×) and brine (1×). The organic layer was dried over MgSO4, filtered and concentrated to give INT 33.

Workup

  1. washwashed with saturated aqueous NaHCO3 (2×), water (2×) and brine (1×)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give INT 33

Sources & evidence

ORD record
ord-f0700dbd998e4009893e292d972e276f
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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