Hydrochloric Acid → HCID 58226385, compound

A solution of N,N′-(1R,1′R)-1,1′-(benzylazanediyl)bis(2-methylpropane-1,1-diyl)bis(1,1,1-trifluoromethanesulfonamide) (81.2 mg, 0.15 mmol, 30 mol %) in CH2Cl2 (1 mL) was treated at rt under N2 slowly with a solution of AlMe3 (10.8 mg, 0.15 mmol) in CH2Cl2 (0.5 mL). The mixture was stirred at room temperature (rt) for 2 h, cooled to −45° C. and treated sequentially with diisopropylethylamine (11 mg, 1.7 equiv), acetyl bromide (117 mg, 1.9 equiv) and 5 (107 mg, 0.500 mmol, 1.0 equiv). The resulting pale yellow solution was stirred for 14 h at −45° C., warmed to rt, and poured into a separatory funnel containing 0.1 N HCl (10) mL). The organic layer was washed with saturated NaHCO3, brine, and dried (Na2SO4). The solvent was removed in vacuo and the yellow oily product was purified by chromatography on SiO2 (4% EtOAc/hexanes to 6% EtOAc/hexanes) to give 6 (99.1 mg, 77%) as a colorless oil: 1H NMR (CDCl3) 4.8-4.65 (m, 1H), 3.60-3.50 (m, 1H), 3.3-3.2 (m, 1H), 3.35, 3.32 (2s, 3H), 3.22-3.08 (m, 1H), 2.18-1.82 (m, 2H) 1.65-1.35 (m, 2H), 1.35-1.20 (m, 14H), 0.90-0.80 (m, 3H).

1. temperaturecooled to −45° C.
2. stirringThe resulting pale yellow solution was stirred for 14 h at −45° C.
3. temperaturewarmed to rt
4. additionpoured into a separatory funnel
5. washThe organic layer was washed with saturated NaHCO3, brine
6. dry with materialdried (Na2SO4)
7. customThe solvent was removed in vacuo
8. customthe yellow oily product was purified by chromatography on SiO2 (4% EtOAc/hexanes to 6% EtOAc/hexanes)

ORD record

ord-9ef92bd949e04c9d99a0082b97af3ee0

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765431B2