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18th May 2012 @ 04:02
Mnr: 11-20

MNR10-1 (0.18 g, 0.38 mmol) in toluene (2 mL) was treated with methanesulfonic acid (0.002 mL, 0.38 mmol) and the reaction was stirred at room temperature for 5 hours by which time TLC had shown complete consumption of SM. The reaction was neutralised with sat. sodium hydrogen carbonate solution, the organic fraction extracted and the aqueous fraction was washed with EtOAc (10 mL x 3). The organic layers were combined, dried, filtered and concentrated to give a white foam.

**after 1 hour it does not look like everything has gone into solution. First TLC at 90 minutes.

TLC after 5 hours in 100% EtOAc

MNR12-6 5 hours

Crude - 0.162 g

FCC - 50-100% EtOAc/Hexane

frac 54-80 0.114 g, 0.31 mmol, 82 % as a white solid

-------------------------------------------------------------- 19/09/12

repeating the conditions but using crude MNR10-3 to see if we can potentially save on doing a 50 g column.

Preparation of the dimethoxy Ugi-intermediate (MNR10-2 and MNR10-3)

MNR10-3 (1.3 g, 2.84 mmol) in toluene (14 mL) was treated with methanesulfonic acid (0.18 mL, 2.84 mmol) and the reaction was stirred at room temperature for 2 hours by which time TLC had shown complete consumption of SM. The reaction was neutralised with sat. sodium hydrogen carbonate solution (15 mL), the organic fraction extracted and the aqueous fraction was washed with EtOAc (20 mL x 3). The organic layers were combined, dried, filtered and concentrated to give a white foam.

TLC of the crude reaction after workup, ran in 75% EtOAc/Hex. Rows, SM, co-spot, Reaction mixture.

MNR12-7_75%EtOA_Hex.JPG

Column - 75-100 EtOAc/Hex

Fracs 11-27 as a of white foam/solid 0.528 g, 1.44 mmol, 51%

test recryst using EtOAc:Hex (10:15 mL)

 

IR 

1d rac IR MNR12-6 dont include.jpg
Attached Files
MNR12-6 5 hours
MNR12-6 scheme.png
MNR12-7 table.PNG
MNR12-7_75%EtOA_Hex.JPG
1d rac IR MNR12-6 dont include.jpg