Trifluoroacetic acid → HCID 86702146, compound

HRID 1776218Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

2-(2,4-Dimethoxybenzyl)-6-fluoro-1,2-thiazinane-1,1-dioxide (0.532 g, 1.8 mmol) in methylene chloride (40 mL) was cooled to 0° C. Trifluoroacetic acid (25 mL) was added and the resultant red solution stirred for 1.5 hrs at 0° C., concentrated under reduced pressure. The crude product was purified by silica gel chromatography (20-70% ethyl acetate/hexanes) to give a clear liquid (0.213 g, 79%). 1H NMR (300 MHz, CDCl3) δ 5.35-5.33 (dd, 0.5H, J=5.0, 2.4 Hz), 5.19-5.17 (t, 0.5H, J=3.6 Hz), 4.76 (br s, 1H), 3.52-3.32 (m, 2H), 2.56-2.40 (m, 2H), 1.91-1.81 (m, 1H), 1.59-1.52 (m, 1H).

Workup

concentrationconcentrated under reduced pressure
customThe crude product was purified by silica gel chromatography (20-70% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-5fd6407faa024e38872c2f78af11042c
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265772B2

Reaction notes

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