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Hazard and Risk Assessment:
As for MNR1-1
MNR28-3
To a cooled solution of MNR27-1 (0.1 g, 0.38 mmol) in DCM (2 mL) at 0°C was added triethylamine (0.0.8 mL, 0.57 mmol) and cyclohexanecarbonyl chloride (0.06 mL, 0.42 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 to give the crude as an orange oil (0.176 g)
Column:- 50-100 EtOAc/PetEther
Fracs 17-26 - 0.063 g, 0.169 mmol, 44% yield (fraction 21 spilt, one of the major fractions)
Characterisation
As a 50:50 mixture of rotamers. Peaks not fully resolved at 300 K
1H NMR (300 MHz, CDCl3): d = 6.73 (s, 1H), 6.65 (s, 1H), 5.17-5.005 (m, 1H), 4.91-4.79 (m, 1H), 4.78-4.67 (m, 1H), 4.50 (s, 0.5H), 4.44 (s, 0.5H), 4.17-4.02 (m, 1H), 3.87 (s, 6H), 3.00-2.63 (m, 4H) 2.48 (t, J = 11.1 Hz, 1H), 1.93-1.20 (m, 10H).
13C NMR (75 MHz, CDCl3): d =174.8, 164.3, 148.3, 148.1, 126.9, 124.4, 111.7, 108.1, 56.1, 55.9, 54.8, 49.0, 45.3, 40.7, 39.1, 29.2, 29.0, 28.2, 25.7.
Chiral HPLC