Trifluoroacetic acid → Ethyl(S-methylsulfonimidoyl)acetate

HRID 1778124Notes

Reaction equation

HRID 1778124 reaction equation
C(OC([N:8]=[S:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH3:11])=[O:10])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][S:9]([CH3:11])(=[NH:8])=[O:10])[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118152570ethyl [N-(tert-butoxycarbonyl)-S-methylsulfonimidoyl]acetate

Product 1

HCID 118152571Ethyl(S-methylsulfonimidoyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl [N-(tert-butoxycarbonyl)-S-methylsulfonimidoyl]acetate in dichloromethane (2.5 mL) was cooled to 0° C. followed by a dropwise addition of trifluoroacetic acid (0.79 mL). The reaction was then stirred at RT for 2 hours. The excess TFA was removed under reduced pressure and the oily residue was partitioned between EtOAc and saturated aq NaHCO3/brine. The organic layer was separated, washed with brine (1×), and dried over Na2SO4. The upper solution layer was decanted and concentrated yielding the title compound as a brown oil (49 mg).

Workup

  1. customThe excess TFA was removed under reduced pressure
  2. customthe oily residue was partitioned between EtOAc and saturated aq NaHCO3/brine
  3. customThe organic layer was separated
  4. washwashed with brine (1×)
  5. dry with materialdried over Na2SO4
  6. customThe upper solution layer was decanted
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5fdff88066e54238963fa789ebdeefba
Source dataset
uspto-grants-2016_02
Patent number
US09266869B2

Reaction notes

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