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29th April 2015 @ 06:54

Procedure:

AEW 223-1 (100 mg, 0.43 mmol, 1 equiv) was added to toluene (2 mL) along with AEW 221-1 (96 mg, 0.43 mmol, 1 equiv), potassium hydroxide (85 mg, 1.52 mmol, 3.5 equiv) and 18-crown-6 (8 mg, 0.03 mmol, 0.07 equiv). The reaction was stirred at room temp for ten minutes (homogeneous orange solution) and then heated to 40°C (bath temperature) for 30 min. TLC showed some SM. Stirred for a further ten min - complete by TLC.

The sample was cooled to room temperature and diluted with 4 mL of water. The mixture was extracted with EtOAc (3 x 10 mL). Fluorescent yellow solution. The combined organic layer was washed with water (1 x 4 mL) until the aqueous layer became neutral followed by brine (3 mL) and dried over Na2SO4. The orange/yellow fluoro solution was filtered and dried under reduced pressure and in vacuo to yield an orange oil that was dried at the high vac.

Crude NMR looks promising. Submitted crude directly to deprotection AEW 130-1.

Data:

TLC 60% EtoAc in Hexane 30 mins:

AEW 228-1 60% EtOAc in Hex 30 mins.JPG

Crude 300 MHz NMR:

AEW 228-1 proton.pdf
AEW 228-1 crude.zip

Hazard and Risk Assessment:


Strings:

InChI=1S/C11H7ClN4/c12-9-6-13-7-10-14-15-11(16(9)10)8-4-2-1-3-5-8/h1-7H

and

InChI=1S/C13H18O3/c14-10-12(11-6-2-1-3-7-11)16-13-8-4-5-9-15-13/h1-3,6-7,12-14H,4-5,8-10H2

to

InChI=1S/C24H24N4O3/c1-3-9-18(10-4-1)20(31-23-13-7-8-14-29-23)17-30-22-16-25-15-21-26-27-24(28(21)22)19-11-5-2-6-12-19/h1-6,9-12,15-16,20,23H,7-8,13-14,17H2

ClC1=CN=CC2=NN=C(C3=CC=CC=C3)N21

and

OCC(OC1OCCCC1)C2=CC=CC=C2

to

C12=NN=C(C3=CC=CC=C3)N1C(OCC(OC4OCCCC4)C5=CC=CC=C5)=CN=C2

Attached Files
AEW 228-1.cdxml
AEW 228-1.png
AEW 228-1 60% EtOAc in Hex 30 mins.JPG
AEW 228-1 proton.pdf
AEW 228-1 crude.zip