Trifluoroacetic acid → HCID 58114486, compound

HRID 1776237Notes

Reaction equation

HRID 1776237 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH2:10][CH2:9][C:8]([F:12])([F:11])[S:7]1(=[O:14])=[O:13].FC(F)(F)C(O)=O>C(Cl)Cl>[F:11][C:8]1([F:12])[S:7](=[O:14])(=[O:13])[NH:6][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86702158HCID 86702158, compound

Product 1

HCID 58114486HCID 58114486, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 2-(2,4-dimethoxybenzyl)-5,5-difluoroisothiazolidine-1,1-dioxide (0.100 g, 0.3 mmol) in methylene chloride (6 mL) was added trifluoroacetic acid (2.182 mL, 29.4 mmol). The resulting red/purple solution was stirred at 0° C. for 3.5 hrs and concentrated in vacuo. The crude material was purified by silica gel chromatography (30-75% ethyl acetate/hexanes) to give a tan oil (0.036 g). 1H NMR (CDCl3, 300 MHz) δ 4.78 (br s, 1H), 3.46-3.40 (q, 2H, J=6.6 Hz), 2.79-2.65 (m, 2H). 19F NMR (CDCl3, 282 MHz)-105.96-106.07 (t, J=15.4 Hz).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude material was purified by silica gel chromatography (30-75% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c80db699f0dd4f1f9c7aee6a004a86dd
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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