Trifluoroacetic acid → HCID 11324510, compound

HRID 2223782Notes

Reaction equation

HRID 2223782 reaction equation
FC(F)(F)C(O)=O.[CH3:8][CH:9]([CH3:32])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])=[CH:15][CH:14]=1>ClCCl>[CH3:8][CH:9]([CH3:32])[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:20][C:21]([OH:23])=[O:22])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11624910HCID 11624910, compound2×

Product 1

HCID 11324510HCID 11324510, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.5 mL) was added in one portion to a stirred solution of 1,1-dimethylethyl N-{4-[(3-methylbutyl)oxy]phenyl}-N-(methylsulfonyl)glycinate (intermediate 7, 140 mg, 0.378 mmol) in dichloromethane (5 mL) at room temperature under an atmosphere of nitrogen. The resulting mixture was stirred for 3 h then the volatiles evaporated. A portion of the crude orange product was purified by reverse phase mass directed preparative HPLC to give the title compound as a white solid (20 mg). LC/MS: 3.22 min; z/e 333, calcd (M+18) 333. 1H NMR (400 MHz; MeOD): 0.95 (6H), 1.75 (2H), 1.85 (1H), 3.05 (3H), 4.05 (2H), 4.35 (2H), 6.90 (2H), 7.40 (2H).

Workup

  1. customthe volatiles evaporated
  2. customA portion of the crude orange product was purified by reverse phase mass

Sources & evidence

ORD record
ord-f29c370855fb41afaf884fc1a5f55fe6
Source dataset
uspto-grants-2008_05
Patent number
US07375248B2

Reaction notes

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