Ammonium Chloride → HCID 58352825, compound

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).

1. temperatureto gradually warm to RT
2. stirringwas stirred at RT for 18 h
3. customThe aqueous layer was separated
4. extractionextracted with EtOAc (100 mL)
5. washThe organic layers were washed with brine (200 mL)
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe product was purified by SiO2 chromatography (200 g, Hexane/EtOAc, 25% to 33%)
10. customto give
11. additionThis mixture of two isomers (6 g)

ORD record

ord-3c49889a2985472090df2cd6d9e1442a

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08361959B2