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Mnr: 21-30
Small scale reaction to test optical purity of the starting MNR3-3 as chiral HPLC can't separate the two.
Hazard and Risk Assessment:
To a cooled solution of R-(+)Praziquanamine (MNR3-3, mmol) in DCM (5 mL) at 0°C was added triethylamine (0.21 mL, 1.48 mmol) and benzoyl chloride(0.13 mL, 1.09 mmol). The solution was stirred overnight at room temperature.
The solution was quenched with water (5 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:- 0.341 g
Column:- 50-100 % EtOAc/Hex
frac 9-13 0.237 g, 0.759 mmol, 77% as white crystals
Characterisation
1H NMR (500 MHz, CDCl3): d= 7. 35-7.41 (m, 5H), 7.29-7.15 (m, 4H), 5,25 (br, 1H), 4.99 (br, 1H), 4.81 (br, 1H), 4.36 (br, 1H), 4.09 (br, 1H), 3.07 (br, 1H), 3.03-2.93 (m, 1H), 2.93-2.84 (m, 1H), 2.83-2.73 (m, 1H).
Chiral HPLC
80:20:0.2 IPA:Hexane:TEA
flow rate 0.35 mL per minute
96.4 % ee
Chiral HPLC mnr24-1
Chiral HPLC MW58
Melting point 119-121 °C
Small scale reaction to test optical purity of the starting MNR3-3 as chiral HPLC can't separate the two.
Hazard and Risk Assessment:
To a cooled solution of R-(+)Praziquanamine (MNR3-3, mmol) in DCM (5 mL) at 0°C was added triethylamine (0.21 mL, 1.48 mmol) and benzoyl chloride(0.13 mL, 1.09 mmol). The solution was stirred overnight at room temperature.
The solution was quenched with water (5 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:- 0.341 g
Column:- 50-100 % EtOAc/Hex
frac 9-13 0.237 g, 0.759 mmol, 77% as white crystals
Characterisation
1H NMR (500 MHz, CDCl3): d= 7. 35-7.41 (m, 5H), 7.29-7.15 (m, 4H), 5,25 (br, 1H), 4.99 (br, 1H), 4.81 (br, 1H), 4.36 (br, 1H), 4.09 (br, 1H), 3.07 (br, 1H), 3.03-2.93 (m, 1H), 2.93-2.84 (m, 1H), 2.83-2.73 (m, 1H).
Chiral HPLC
80:20:0.2 IPA:Hexane:TEA
flow rate 0.35 mL per minute
96.4 % ee
Chiral HPLC mnr24-1
Chiral HPLC MW58
Melting point 119-121 °C
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