Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 57467605, compound

HRID 404368Notes

Reaction equation

[CH3:1][C:2]1([CH3:25])[C:6]([C:7]2[C:8]([O:18]C3CCCCO3)=[CH:9][C:10]([F:17])=[C:11]([CH:16]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH2:4][CH2:3]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[CH3:1][C:2]1([CH3:25])[C:6]([C:7]2[C:8]([OH:18])=[CH:9][C:10]([F:17])=[C:11]([CH:16]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred mixture of T31.4 (5.65 g, 16.2 mmol) in MeOH (60 mL) was added PPTS (0.42 g, 1.69 mmol). The mixture was heated to 50° C. and monitored with TLC and LCMS. After 19 hours, the organic solvent was removed under reduced pressure, and the residue was then purified on silica gel (0-15% EtOAc in hexanes) to yield T31.5 as a white solid (3.47 g, 81% yield). 1H NMR (500 MHz, CDCl3) δ ppm 7.69 (1H, d, J=8.3 Hz), 6.71 (1H, d, J=12.0 Hz), 5.93 (1H, d, J=1.7 Hz), 5.80 (1H, t, J=2.4 Hz), 3.90 (3H, s), 2.54 (2H, m), 1.93 (2H, t, J=7.1 Hz), 1.11 (6H, s).

Workup

customthe organic solvent was removed under reduced pressure
customthe residue was then purified on silica gel (0-15% EtOAc in hexanes)

Sources & evidence

ORD record: ord-72e6cd74c3714947ac975d46ab2bac24
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748462B2

Reaction notes

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