Ammonium Chloride → HCID 58352825, compound

Participants

Reaction Steps

Magnesium turnings (2.21 g, 90.9 mmol) were stirred with a magnetic stir bar overnight in a 500 ml round-bottom flask. Anhydrous ethyl ether 9173 ml) was added. 1-Bromo-5-methylhexane (15.0 g, 90.9 mmol) was added dropwise over 40 minutes. The solution was stirred at RT for 3.5 hours. The grignard solution was added to (S)-isopropyl 4-((tert-butylsulfinylimino)methyl)benzoate (13.4 g, 45.4 mmol) in 100 mL anhydrous DCM at −48° C. The solution was allowed to gradually warm to RT and was stirred at RT for 18 h. Saturated NH4Cl (150 ml) and EtOAc (200 mL) were added. The aqueous layer was separated and extracted with EtOAc (100 mL). The organic layers were washed with brine (200 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The product was purified by SiO2 chromatography (200 g, Hexane/EtOAc, 25% to 33%) to give a mixture of R isomer and S isomer of isopropyl 4-(1-((S)-1,1-dimethylethylsulfinamido)-6-methylheptyl)benzoate (14.8 g, 82.4%, R:S=2:1). This mixture of two isomers (6 g) was resolved by Chiralpak AD column (4% isopropyl alcohol in hexane) to give isopropyl 4-((R)-1-((S)-1,1-dimethylethylsulfinamido)-6-methylheptyl)benzoate (2.61 g).

Provenance & Evidence