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21st June 2012 @ 02:46
Mnr: 31-40

Hazard and Risk Assessment:

ProcedureTo a cooled solution of MNR30-7(0.09 g g, 0.34 mmol) in DCM (2 mL) at 0°C was added triethylamine (0.05 mL, 0.51 mmol) and benzoyl chloride (0.05 mL, 0.38 mmol). The solution was stirred for XX hours at room temperature.

(on at 11am 21/6/12)

TLC after 8 hours show slight trace of SM so reaction was left overnight

First TLC plate in 100% EtOAc. mnr38-1, mnr30-7, mnr39-1 Second TLC plate 20% MeOH/EtoAc. mnr30-7, co, mnr39-1, co, mnr12-1

SANY0200.JPG

In the morning, the reaction was quenched with water (3 mL) and stirred for 30 minutes then the organic layer was separated and washed with sodium carbonate solution (5 mL), 1M HCl (5 ml) and brine (5 mL), dried and filtered to give the crude as an orange oil (0.156 g)

The crude was then purified by FCC (50-100% EtOAc/Hex)

Fracs 38-60 0.046 g as a white solid - original nmr contained EtOAc but after taking the product up in DCM and putting under the high vac the product was recovered as a clean white solid

NMR

mnr39-1_1H.pdf
mnr39-1_frac38-60.zip

1H NMR (500 MHz, CDCl3): d = 7.49-7.39 (m, 5H), 6.78 (br, 1H), 6.62 (s, 1H), 5.17 (br, 1H), 4.95-4.75 (m, 2H), 4.33 (br, 1H), 4.14-4.02 (m, 1H), 3.84 (br, 6H), 3.03 (br, 1H), 2.95-2.73 (m, 2H), 2.73-2.59 (m, 1H).

mnr39-1_13C.pdf
mnr39-1_13C_zoom.pdf
mnr39-1_frac38-60.zip

13C NMR (125 MHz, CDCl3): d = 170.3, 164.2, 148.4, 148.1, 134.2, 130.7, 128.7, 127.4, 127.1, 124.4, 111.8, 108.2, 56.2, 55.9, 54.5, 51.4, 46.1, 39.1, 28.3.

Chiral HPLC- 99% ee using the CHIRALCEL OD-H column, 25% EtOH:Hex with 0.1% TEA and a flow rate of 0.75 mL/min

mnr39-1_25EtOH_075ml_23June.pdf

melting point - 104-106 °C

IR 

1d S IR MNR39-1 dont include.jpg
Attached Files
21st June 2012 @ 02:36
Mnr: 31-40

Hazard and Risk Assessment: As for MNR1-1

ProcedureTo a cooled solution of MNR30-7(0.10 g g, 0.38 mmol) in DCM (2 mL) at 0°C was added triethylamine (0.06 mL, 0.57 mmol) and cyclohexanecarbonyl chloride (0.06 mL, 0.42 mmol). The solution was stirred for a total of 22 hours at room temperature.

(on at 11am 21/6/12)

In the morning, the reaction was quenched with water (3 mL) and stirred for 30 minutes then the organic layer was separated and washed with sodium carbonate solution (5 mL), 1M HCl (5 ml) and brine (5 mL), dried and filtered to give the crude as an orange oil (0.165 g)

The crude was then purified by FCC (50-100% EtOAc/Hex)

Fracs 35-51 0.053 g as a white solid - original nmr contained EtOAc but after taking the product up in DCM and putting under the high vac the product was recovered as a clean white solid

NMR

mnr38-1_1H.pdf
mnr38-1_frac35-51.zip

1H NMR (500 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).

mnr38-1_13C.pdf
mnr38-1_frac35-51.zip

13C NMR (125 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, 25.6.

Chiral HPLC - 99% ee using the CHIRALCEL OD-H column, 25% EtOH:Hex with 0.1% TEA and a flow rate of 0.5 mL/min

mnr38-1_25EtOH_05ml_24June.pdf

IR 

1b S IR MNR38-1.jpg
Attached Files