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Example 1

NH4OAc (316 mg, 4.10 mmol) was added to a solution of the SM (2.00 g, 6.84 mmol) in nitromethane (517 mL). The reaction mixture was stirred at 60 C for 18 h. The mixture was quenched with H2O and DCM was added. The layers were separated and the org layer was washed with brine, dried (MgSO4), and concentrated to give an orange oil. The material (1.8 g) was purified by Prep LC (50 g silica, 0-5% EtOAc/heptane) to provide the product as a yellow oil. [750 mg, 33%]

[Patent Reference: WO2015144799, 340, (18.8 MB)]

Example 2

A mixture of the SM (150 g, 0.999 mol) and NH4OAc (30.8 g, 0.40 mol) in nitromethane (1.5 L) was refluxed for 16 h. The mixture was concentrated then diluted with EtOAc (1.0 L) and washed sequentially with H2O (1.0 L) followed by brine (100 mL). The org layer was dried (Na2SO4) and concentrated. The resulting material was triturated with 10:1 PE/EtOAc for 10 min and the solids were collected by filtration to provide the product as a yellow solid. [80 g, 42%]

[Patent Reference: WO2016014463, page 94, (6.7 MB)]