Trifluoroacetic acid → HCID 58114513, compound

HRID 1776220Notes

Reaction equation

HRID 1776220 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH2:11][CH2:10][CH2:9][C:8]([F:13])([F:12])[S:7]1(=[O:15])=[O:14].FC(F)(F)C(O)=O>C(Cl)Cl>[F:12][C:8]1([F:13])[S:7](=[O:15])(=[O:14])[NH:6][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86702148HCID 86702148, compound

Product 1

HCID 58114513HCID 58114513, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,4-dimethoxybenzyl)-6,6-difluoro-1,2-thiazinane-1,1-dioxide (0.090 g, 0.3 mmol) in methylene chloride (7 mL) was added trifluoroacetic acid (4 mL), and the resultant red solution stirred for 3 hrs at room temperature. The mixture was concentrated in vacuo to afford the crude residue. The crude product was purified by silica gel chromatography (10-60% ethyl acetate/hexanes) to give a clear oil (0.034 g). 1H NMR (CDCl3, 300 MHz) δ 4.85 (br s, 1H), 3.46-3.40 (m, 2H), 2.60-2.47 (m, 2H), 2.01-1.93 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto afford the crude residue
  3. customThe crude product was purified by silica gel chromatography (10-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-45a2914f63f54ab9b6324e339380d87c
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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