Hydrochloric Acid → (S)-1-(4-(tert-butyl)phenyl)ethanaminium chloride

HRID 1851884Notes

Reaction equation

HRID 1851884 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13][S@@](C(C)(C)C)=O)[CH3:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[ClH:20]>CO>[Cl-:20].[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]([NH3+:13])[CH3:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71074743(R)-N-((S)-1-(4-(tert-butyl)phenyl)ethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 86674539(S)-1-(4-(tert-butyl)phenyl)ethanaminium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)—N—((S)-1-(4-(tert-butyl)phenyl)ethyl)-2-methylpropane-2-sulfinamide (977 mg) in MeOH (1.75 mL) was added conc. HCl (1.75 mL). The reaction was aged at room temperature monitoring disappearance of starting material by analytical reverse-phase HPLC. When the starting material was consumed, the reaction was concentrated in vacuo. The crude residue was resuspended in MeOH (1 mL) and crashed out of solution by the addition of Et2O. Filtration afforded the title compound as a colorless solid (559 mg). ESI-MS (m/z): 161 [M+H—NH3]+, 338 [2M+H—NH3]+

Workup

  1. customwas aged at room temperature
  2. customWhen the starting material was consumed
  3. concentrationthe reaction was concentrated in vacuo
  4. additioncrashed out of solution by the addition of Et2O
  5. filtrationFiltration

Sources & evidence

ORD record
ord-64b6db82b7824ced9eae095d8db5da56
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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