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12th May 2014 @ 01:24

To a solution of N1,N3-bis((R)-2-hydroxy-1-phenylethyl)-2,2-dimethylmalonamide (KAB 101) (125 mg, 0.34 mol) in CH­2Cl­2 (3 mL) at –78 °C was added (diethylamino)sulfur trifluoride (0.13 mL, 1.01 mmol). 

After stirring at room temp. for 30 min, CH2Cl2 (10 mL) was added, the mixture was washed with saturated aqueous NaHCO3 (5 mL) and the aqueous layer was extracted with CH2Cl2 (10 mL). The combined organic layers were washed with saturated aqueous H2O (5 mL), the aqueous layer was extracted with CH2Cl2 (5 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo to yield the crude product as a yellow oil. Crude 1H NMR looked good.

Purification by column chromatography (EtOAc/heptane, 1:3 to 1:2) resulted in isolation of 

Data:

Crude NMR 200 MHz

AEW 147-1 crude 200mhz.pdf
AEW 147-1 cat.zip

Hazard and Risk Assessment:

HIRAC AEW 147-1.pdf

InChi:

InChI=1S/C21H26N2O4/c1-21(2,19(26)22-17(13-24)15-9-5-3-6-10-15)20(27)23-18(14-25)16-11-7-4-8-12-16/h3-12,17-18,24-25H,13-14H2,1-2H3,(H,22,26)(H,23,27)

to

InChI=1S/C21H22N2O2/c1-21(2,19-22-17(13-24-19)15-9-5-3-6-10-15)20-23-18(14-25-20)16-11-7-4-8-12-16/h3-12,17-18H,13-14H2,1-2H3

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Attached Files
AEW 147-1.png
AEW 147-1.cdxml
AEW 147-1 crude 200mhz.pdf
AEW 147-1 cat.zip
HIRAC AEW 147-1.pdf