All Notebooks | Help | Support | About
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

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

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).

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

melting point - 104-106 °C

IR