Trifluoroacetic acid → N-((2R)-2-methylamino-3-phenylpropyl)methansulfonamide

HRID 1601998Notes

Reaction equation

HRID 1601998 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([C@H:16]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:17][NH:18][S:19]([CH3:22])(=[O:21])=[O:20])C)(C)(C)C>ClCCl>[CH3:13][NH:14][C@H:16]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:17][NH:18][S:19]([CH3:22])(=[O:20])=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54199950N-((1R)-1-Benzyl-2-((methylsulfonyl)amino)ethyl)-N-methylcarbamic acid tert-butylester

Product 1

HCID 54473398N-((2R)-2-methylamino-3-phenylpropyl)methansulfonamideYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., trifluoroacetic acid (5 ml) was added to a solution of N-((1R)-1-benzyl-2-((methylsulfonyl)amino)ethyl)-N-methylcarbamic acid tert-butylester (913 mg, 2.67 mmol) in dichloromethane (5 ml). The reaction mixture was stirred for 15 min at 0° C. The solvent was removed in vacuo without warming. The residue was dissolved in dichloromethane (50 ml) and the solvent was removed in vacuo. The latter procedure was repeated two times. The crude product was purified by flash chromatography on silica (20 g), using dichloromethane/methanol/25% aqueous ammonia as eluent, to give 658 mg of N-((2R)-2-methylamino-3-phenylpropyl)methansulfonamide.

Workup

  1. customThe solvent was removed in vacuo
  2. temperaturewithout warming
  3. dissolutionThe residue was dissolved in dichloromethane (50 ml)
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by flash chromatography on silica (20 g)

Sources & evidence

ORD record
ord-a80e089cad2b4efb837b9ddbaa41cdbd
Source dataset
uspto-grants-1999_11
Patent number
US05977178

Reaction notes

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