Trifluoroacetic acid → HCID 57961660, compound

HRID 541938Notes

Reaction equation

HRID 541938 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[CH2:7][S:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([NH:17]C(=O)OC(C)(C)C)[CH:14]=[CH:15][CH:16]=1)([O-:3])=[O:2].FC(F)(F)C(O)=O>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[CH2:7][S:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[NH2:17])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57962670HCID 57962670, compound

Product 1

HCID 57961660HCID 57961660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (3-{2-[(3-nitrobenzyl)thio]ethyl}phenyl)carbamate (0.38 g, 0.97 mmol) in dichloromethane (2 mL) was treated with trifluoroacetic acid and stirred for 30 min. The reaction mixture was concentrated and poured into 10% potassium carbonate (30 mL) and ethyl acetate (100 mL). The organic layer was separated, washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give the desired product as a crude orange oil. This material was purified by flash column chromatography to give the desired product (0.19 g, 67%) as an orange oil. LCMS for C15H17N2O2S (M+H)+: m/z=289.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into 10% potassium carbonate (30 mL) and ethyl acetate (100 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (25 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-86da7c7124264d4496d9da3ff30117c7
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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