Pyridine → HCID 57067061, compound

HRID 1284874Notes

Reaction equation

N1C=CC=CC=1.FC(F)(F)S([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])(=O)=O.[F:22][C:23]([F:49])([CH2:26][C@H:27]([C@@H:29]1[C@:46]2([CH3:47])[C@H:32]([C@H:33]3[C@H:43]([CH2:44][CH2:45]2)[C@:41]2([CH3:42])[C:36]([CH2:37][C@@H:38]([OH:48])[CH2:39][CH2:40]2)=[CH:35][CH2:34]3)[CH2:31][CH2:30]1)[CH3:28])[CH2:24]O>ClCCl>[F:22][C:23]([F:49])([CH2:26][C@H:27]([C@@H:29]1[C@:46]2([CH3:47])[C@H:32]([C@H:33]3[C@H:43]([CH2:44][CH2:45]2)[C@:41]2([CH3:42])[C:36]([CH2:37][C@@H:38]([OH:48])[CH2:39][CH2:40]2)=[CH:35][CH2:34]3)[CH2:31][CH2:30]1)[CH3:28])[CH2:24][O:12][S:13]([C:16]([F:17])([F:18])[F:19])(=[O:14])=[O:15]

Participants

Conditions

Temperature: -20 °C

Procedure

The mixture of pyridine (124 μl) and trifluoromethanesulfonic anhydride (206 μl) in dichloromethane (5 ml) was stirred at -20° C. under argon atmosphere for 5 min. To this solution the alcohol (7) (400 mg, 1.02 mmol) in dichloromethane (10 ml) was added and the mixture was stirred at room temperature for 40 min. The usual work-up (dichloromethane for extraction) gave the triflate (8) (612 mg), which was used in the next step without further purification. 1H-NMR δ: 0.73 (3H, s, 18-H3), 1.00 (3H, s, 19-H3), 1.15 (3H, d, J=6 Hz, 21-H3), 3.56 (2H, m, THP), 3.85 (1H, m, 3-H), 4.50 (2H, t, J=12 Hz, 24-H2), 4.70 (1H, m, THP), 5.37 (1H, m, 6-H). 19F-NMR δ: +12.2 (3F), +41.3 (2F).

Workup

stirringthe mixture was stirred at room temperature for 40 min
extractionThe usual work-up (dichloromethane for extraction)

Sources & evidence

ORD record: ord-67ec3b638b5e41ecabb0db51eb36e8ee
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04564474

Reaction notes

Loading…