Trifluoromethanesulfonic acid → HCID 131735199, compound

HRID 625183Notes

Reaction equation

OS(C(F)(F)F)(=O)=O.[Cl-:9].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S+:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:20]3[CH:27]=[CH:28][CH:29]=[CH:30][C:19]2=3)=[CH:14][C:13]=1[CH2:31][C:32]([O:34][CH2:35][C:36]([O:38]C1(C)C2CC3CC(CC1C3)C2)=[O:37])=[O:33]>C(Cl)Cl>[Cl-:9].[C:36]([CH2:35][O:34][C:32](=[O:33])[CH2:31][C:13]1[CH:14]=[C:15]([S+:18]2[C:19]3[CH:30]=[CH:29][CH:28]=[CH:27][C:20]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]2=3)[CH:16]=[CH:17][C:12]=1[O:11][CH3:10])([OH:38])=[O:37]

Participants

Conditions

Temperature: 25 °C

Procedure

Triflic acid (trifluoromethansulfonic acid) (0.5 mL) was added to a solution of 5-(4-methoxy-3-(2-(2-((2-methyladamantan-2-yl)oxy)-2-oxoethoxy)-2-oxoethyl)phenyl)-dibenzothiophenium chloride (3.00 g, 5.07 mmol) in DCM (50 mL) and stirred at 25° C. for 48 h. The precipitate was filtered, washed with MTBE:Acetone (50 mL) and MTBE (2×100 mL) to afford the title compound (2.05 g, 91%) as a white solid. 1H NMR (300 MHz, (CD3)2SO) δ: 12.5 (brs, COOH), 8.52 (d, J=7.8 Hz, 2H), 8.29 (d, J=8.1 Hz, 2H), 7.95 (t, J=7.5 Hz, 2H), 7.67-7.79 (m, 3H), 7.38 (vis s, 1H), 7.22 (d, J=8.1 Hz, 1H), 4.51 (s, 2H), 3.81 (s, 3H), 3.66 (s, 2H).

Workup

filtrationThe precipitate was filtered
washwashed with MTBE

Sources & evidence

ORD record: ord-8f8ba9effd414e74b907f4ca60bf80cd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09304394B2

Reaction notes

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