2,4,6-Trimethylpyridine → N,N-Bis-(2-trifluoromethanesulfonyloxyethyl)-2-nitrobenzenesulfonamide

HRID 2276937Notes

Reaction equation

S([O:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])(C(F)(F)F)(=O)=O.[OH:16][CH2:17][CH2:18][N:19]([CH2:32][CH2:33]O)[S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N+:29]([O-:31])=[O:30])(=[O:22])=[O:21].N1C(C)=CC(C)=CC=1C>C(Cl)Cl.C(Cl)(Cl)Cl>[F:13][C:12]([F:15])([F:14])[S:9]([O:16][CH2:17][CH2:18][N:19]([CH2:32][CH2:33][O:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11])[S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N+:29]([O-:31])=[O:30])(=[O:22])=[O:21])(=[O:10])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

Triflic anhydride (13.6 g, 48.3 mmol) was added dropwise with stirring to a 0° C. solution of N,N-bis-(2-hydroxyethyl)-2-nitrobenzenesulfonamide (7.00 g, 24.1 mmol) from Example 16A and 2,4,6-collidine (5.85 g, 48.3 mmol) in anhydrous methylene chloride (50 mL) (J. A. Kozlowski, et al., Bioorg. Med. Chem. Lett. 12: 791-794, 2002). Reaction stirred two hours at 0° C. and then overnight at room temperature. Reaction diluted with chloroform, washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by normal phase HPLC on a Biotage pre-packed silica gel column cluting with 3:1 hexane:ethyl acetate to afford the title compound. MS (ESI) m/z 555 (M+H)+.

Workup

customReaction
customovernight
customat room temperature
customReaction
washwashed with saturated NaHCO3 and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by normal phase HPLC on a Biotage pre-packed silica gel column

Sources & evidence

ORD record: ord-e829230a7f2b4873a3795c2285fc97a2
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133145B2

Reaction notes

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