KBS12-2 - Click coupling of azidoadamantane and bis-propargyl cyclam CONTINUED FROM HONOURS

[KlementineJBS]

Continuation from Honours work.

Link to HIRAC and original method.

Reaction scheme

[KlementineJBS]

24.08.22

1. Dissolved product in DCM (15 mL)
2. Washed with buffer solution (15 mL of 50 mmol EDTA in ammonium chloride/ammonia buffer, pH 10) + water (10 mL)
3. Washed with buffer solution (30 mL, as above)
4. Washed with buffer solution (15 mL, as above) and brine (10 mL)

Aqueous layer was turning faintly blue but DCM layer remained stubbornly green.

5. Transferred DCM layer to RBF and added 30 mL buffer solution. Heated to 40 C with stirring from 11.30 am

Empty vial: 15.8517 Full vial: 16.4258 Mass: 574.1 mg

[KlementineJBS]

26.08.22

NMR

1H NMR (300 MHz, CDCl3) δ 5.30, 3.78, 3.33, 2.59, 2.47, 2.23, 1.79, 1.60, 1.41.

KBS12-2.zip KBS12-2 processed.pdf

Peak assignation not yet complete, but appears identical (if more concentrated) to previous attempt, KBS12-1.

[KlementineJBS]

06.09.22

Rf value

Rf = 0.51 (2.0/3.9) in 10:90 MeOH:DCM

[KlementineJBS]

12.09.22

Found a vial labelled "KBS12-2 extra" - applying same process of removing copper using EDTA buffer (product was a green oil/gel).

~ 5 mL DCM and 8 mL EDTA buffer left stirring from 10.50 am

Removed buffer by pipette and added ~5 mL fresh. Repeated this once more then extracted with a sep funnel.

Empty vial: 16.0582 Full vial: 16.1047 Mass: 46.5 mg

[KlementineJBS]

19.09.22

Have been trying to "clean up" sample for characterisation via trituration.

KBS12-2 19-09-22_1.zip KBS12-2 19-09-22 processed.pdf

Still contains impurities at 0.86 and 1.26 - likely either grease or hexane.

[KlementineJBS]

LRMS

20210429KBS12-1.d (2).zip KBS12.pdf