Comments (12)
07.09.22
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Dissolved *KBS12-2 (#30) (467 mg, 0.562 mmol) in dioxane (6 mL)
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Added 3 drops water (more than needed - intended to add 1)
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Added this solution to ice-cold HCl (4 M in dioxane, 0.5 mL, 2.00 mmol) at 4.05 pm
NOTE: some solution spilled in transfer
- Allowed to warm to rt while stirring
TLC at 5 pm was inconclusive - product thought to be lowest Rf spot down the bottom (see previous attempt but unsure of why four spots appear. Previously, only top spot was seen - however, in #30, product appears around middle of TLC plate. Solvent system differed by addition of ammonium.
Eluent is 9:1:90 MeOH/NH4/DCM
from usyd_phd_eln.
08.09.22
TLC at 11 am still indicates reaction is not complete.
- Added additional HCl (4 M, 0.5 mL, 2.00 mmol)
TLC at 1.30 pm indicated reaction was complete.
- Removed dioxane via rotary evaporation and transferred to vial.
Empty vial: 15.9174
Full vial: 16.2568
Mass: 339.4 mg
12.09.23 full vial: 16.1573
Mass: 239.9 mg
from usyd_phd_eln.
09.09.22
LRMS
Peak at 631.49 [M+H]+.
KBS13-3 cr.d.zip
KBS13-3 cr.pdf
Procedure
Converted some of product to free base for characterisation.
- 100 mg product was dissolved in water (5 mL) and sodium hydroxide solution (2.5 M, 1 mL) was added.
- Extracted with DCM (3 x 10 mL)
- Rotovapped down and hivac'd to obtain swamp brown foam
Empty vial: 15.6804
Full vial: 15.7508
Mass: 70.4 mg (0.112 mmol), 79%
H NMR
21.1 mg in chloroform
KBS13-3 FB_1.zip
KBS13-3 FB processed.pdf
(pdf includes comparison with 13-2 made last year)
Appears to be the same product.
from usyd_phd_eln.
12.09.22
Wanted to clean up free base so triturated with hexane. Accidentally used low-grade hexane first so repeated with spectroscopy grade hexane again afterwards (3 x 2 mL). Left on hi vac overnight.
from usyd_phd_eln.
13.09.22
NMR of free base after trituration looks cleaner, but with lingering hexane peaks. (Pdf contains triturated sample spectrum overlaid against previous sample spectrum.)
KBS13-3 FB 13-09-22_1.zip
KBS13-3 FB 13-09-22 processed.pdf
Will hi vac overnight again and do quantitative NMR.
from usyd_phd_eln.
14.09.22
KBS13-3 FB 14-09-22_1.zip
KBS13-3 FB 14-09-22 processed.pdf
NMR is cleaner, need to do quantitative. This sample was 20.3 mg.
from usyd_phd_eln.
16.01.23
Decided to pass some of the remaining HCl salt through a C18 column to purify as quantitative NMR suggested that the FB sample was < 95 % pure.
from usyd_phd_eln.
17.01.23
Letter | Fractions | Empty vial weight | Mass | LRMS |
---|---|---|---|---|
A | 1-2 | - | - | KBS13-3 HCl salt RP A.pdf |
B | 3-5 | - | - | KBS13-3 HCl salt RP B.pdf |
C | 6-8 | - | - | N/A |
D | 9-10 | - | - | KBS13-3 HCl salt RP D.pdf |
E | 11-16 | - | - | KBS13-3 HCl salt RP E.pdf |
KBS13-3 HCl salt RP A B D E.zip
H NMR
KBS13-3 HCl salt reverse phase.pdf
KBS13-3 Hcl A_1.zip
KBS13-3 Hcl B_1.zip
KBS13-3 Hcl C_1.zip
KBS13-3 Hcl D_1.zip
KBS13-3 Hcl E_1.zip
All NMR spectra appear very similar but with subtle changes. Given that each sample ionised identically, it seems possible that the different fractions correspond to different ionisation states e.g. +1, +2.
Note that B and C have identical spectra.
from usyd_phd_eln.
18.01.23
Combined all five fractions and converted to free base using Ambersep 900.
Combined fractions were white and powdery with a combined mass of 127.4 mg.
Unpurified HCl salt (left) and purified HCl salt fractions (right):
- Rinsed 2 spatulas of ambersep with methanol (x 3)
- pre-swelled with methanol (~ 5 mL)
- Added clean HCl salt (127.4 mg) dissolved in methanol (~ 15 mL)
- Left stirring for ~50 minutes
- Filtered with a Buchner funnel
- Rotovapped down and hi-vacced
Note that conversion to free base can be seen on TLC - this was run in 90% DCM, 9% methanol, 1% ammonium hydroxide.
from usyd_phd_eln.
23.01.23
After Ambersep:
Empty vial: 15.8195
Full vial: 15.9091
Mass: 89.6 mg
Put FB through an aluminum oxide plug - layered a small sintered funnel with filter paper, 3 cm neutral aluminium oxide and another filter paper. Applied vacuum and added enough ethyl acetate to wet all the aluminium oxide.
Added KBS13-3 FB (89.6 mg) dissolved in ethyl acetate and methanol, washed through with 1:9:90 ammonium hydroxide: methanol: DCM (3 x 10 mL). Rotovapped down filtrate.
Empty vial: 15.8089
Full vial: 15.8850
Mass: 76.1 mg
H NMR
Doesn't seem to be any cleaner than previous samples.
KBS13-3 FB 23-01-23_1.zip
KBS13-3 FB 23-01-23.pdf
from usyd_phd_eln.
from usyd_phd_eln.
Prep HPLC
from usyd_phd_eln.
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