Hydrochloric Acid → HCID 59699472, compound

Reaction equation

[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][F:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[O:6]C(C2C=CC=CC=2)=[N:4]1.Cl.C(OCC)(=O)C>ClCCl>[NH2:4][C@H:3]([CH2:2][F:1])[C@@H:7]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH2:17][F:18])(=[O:16])=[O:15])=[CH:12][CH:13]=1)[OH:6]

Participants

Procedure

A solution of sulfone 22 (1.47 g, 4.19 mmol) in dichloromethane (50 mL) was mixed with 6N HCl (40 mL). Dichloromethane was distilled out and the resulting white suspension was stirred at reflux for 14 hours. It was cooled to room temperature and treated with aqueous NaHCO3 to pH=8˜9. Extraction with dichloromethane (3×50 mL) afforded an oil residue which was subjected to flash chromatography (SiO2, hexanes/ethyl acetate=2:1 to ethyl acetate 100%) to provide 10 g of the desired product, as a light yellow oil. 1H NMR (400 MHz, CDCl3) 3.05-3.15 (m, 1H), 4.24-4.52 (m, 2H), 4.72 (d, J=6 Hz, 1H), 5.09 (s, 1H), 5.21 (s, 1H), 7.62 (d, J=9 Hz, 2H), 7.93 (d, J=9 Hz, 2H).