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For formation of the N-cyclohexanoyl final product to check the ee of the resolution by HPLC.
Hazard and Risk Assessment:
As for MNR1-1
MNR28-1
To a cooled solution of MNR27-14 (0.032 g, 0.12 mmol) in DCM (1 mL) at 0°C was added triethylamine (0.03 mL, 0.18 mmol) and cyclohexanecarbonyl chloride (0.02 mL, 0.13 mmol). The solution was stirred overnight at room temperature.
The solution was quenched with water (2 mL) and stirred for a further 30 min. The layers were separated and the organic layer was washed with saturated sodium carbonate solution (5 mL), 0.5 M HCl (5 mL) and brine (5 mL). Dried over magnesium sulfate, filtered and concentrated under reduced pressure.
Crude as a yellow oil: 0.108 g.
The crude oil was purified by FCC (50-100 % EtOAc/hexane).
Frac 16-25 - 0.034 g, as an off white solid.
Not totally pure by NMR but ran chiral HPLC to determine the ee 17 % (sample was very dilute but this was just a quick experiment to determine if the resolution was a success or not.)
MNR28-2
To a cooled solution of MNR27-20 (0.036 g, 0.14 mmol) in DCM (1 mL) at 0°C was added triethylamine (0.03 mL, 0.18 mmol) and cyclohexanecarbonyl chloride (0.02 mL, 0.13 mmol). The solution was stirred overnight at room temperature.
The solution was quenched with water (2 mL) and stirred for a further 30 min. The layers were separated and the organic layer was washed with saturated sodium carbonate solution (5 mL), 0.5 M HCl (5 mL) and brine (5 mL). Dried over magnesium sulfate, filtered and concentrated under reduced pressure.
Crude as a yellow oil: 0.053g.
The crude oil was purified by FCC (50-100 % EtOAc/hexane).
Frac 14-22 - 0.035 g, as an off white solid.
Not totally pure by NMR but ran chiral HPLC to determine the ee 12 % (sample was very dilute but this was just a quick experiment to determine if the resolution was a success or not.)
IR