Comments (13)
KBS17 (122.9 mg, 0.313 mmol) needs 0.72 mmol azidoadamantane (127.6 mg)
Copper: 0.0626 mmol = 15.6 mg
Sodium ascorbate: 0.1565 mmol = 31.0 mg
- Added azidoadamantane, copper sulfate and sodium ascorbate to RBF.
- Evacuated and filled with nitrogen (x 3)
- Added KBS17 (#22) - 122.9 mg, 0.313 mmol - via solution transfer with sparged THF (6 mL)
- Added sparged water (5 mL)
- Left stirring from Monday afternoon until Thursday afternoon - probably unnecessarily long but delayed by strike action
Tuesday morning
from usyd_phd_eln.
18.08.22
TLC indicated completion - azide didn't show up well but has an Rf just slightly lower than the RM spot.
BP = bis-propargyl amine, RM = reaction mixture, AA = azidoadamantane. Unmarked spots are cospots of the two adjacent compounds. Run in 4.5% MeOH : 0.5% NH4 : 95% DCM.
- Added ammonium chloride solution (Sat., 5 mL)
- Extracted with DCM (3 x 10 mL)
- Washed with brine (~15 mL)
- Dried over MgSO4 and rotovapped
Empty vial: 16.1107
Full vial: 16.3665
Mass: 255.8
from usyd_phd_eln.
22.08.22
LRMS
Peaks at 747.54 [M+H], 769.51 [M+Na].
KBS22-1 cr.d.zip
KBS22-1 cr.pdf
H NMR
KBS22-1 cr_1.zip
KBS22-1 cr processed.pdf
from usyd_phd_eln.
07.09.22
Needed to column crude product - ran TLC's to determine solvent system.
Fractions | Empty vial | Full vial | Mass (mg) | Moles | % | Product |
---|---|---|---|---|---|---|
2 | - | - | - | - | - | Unseparated crude product |
3-4 | 15.8771 | 15.8912 | 14.1 | 0.0189 | 6 | Product |
5-10 | 15.9034 | 15.9518 | 48.4 | 0.0648 | 21 | Product |
H NMR
KBS22-2 F5+_1.zip
KBS22-2 F3-4_1.zip
KBS22-1 F3-10 processed.pdf
from usyd_phd_eln.
08.09.22
Recolumned but had same issue - compound shot straight through column.
Kept fractions and 5 and 6 and decided to column a third time with ethyl acetate and hexane. Solvent system of 20 - 40% ethyl acetate was determined upon by TLC.
from usyd_phd_eln.
09.09.22
from usyd_phd_eln.
12.09.22
TLC'd fractions again after the weekend.
Believed bottom spot to be product, so only isolated select fractions.
Fractions | Empty vial | Full vial | Mass (mg) | Moles | % | Species |
---|---|---|---|---|---|---|
3 | 15.8309 | 15.8374 | 6.5 | - | - | Azidoadamantane |
1,2,4-6, 11-17 | 15.8090 | 15.8732 | 64.2 | - | - | Mixture |
18-19 | 15.7425 | 15.7447 | 2.2 | - | - | Unknown |
20-25 | 15.5487 | 15.5607 | 12 | 0.016 | 5 | Presumed product, unclean |
Column flush | 15.7096 | 15.8169 | 107.3 | 0.144 | 46 | Presumed product |
H NMR
KBS22-1 C3 F20-25_1.zip
KBS22-1 C3 flush_1.zip
KBS22-1 C3 F3_1.zip
KBS22-1 C3 F3, F20-25, flush processed.pdf
TLC showing pooled fractions on left and flush on right, eluent = 30/70 ethyl acetate/hexanes, flush Rf = 0.24
from usyd_phd_eln.
14.09.22
LRMS
KBS22-1 C3 pooled fractions.d.zip
KBS22-1 C3 pooled fractions.pdf
Peaks at 429.36, 445.36, 543.42
KBS22-1 C3 flush.d.zip
KBS22-1 C3 flush.pdf
Peaks at 747.56 [M+H]+, 769.53 [M+Na]+
from usyd_phd_eln.
15.09.22
Did a hexane wash (3 x 2 mL spectroscopic grade hexane) of 22-1 and hi-vacced overnight. Some solvent (ethyl acetate, hexane?) or potentially grease remaining - will repeat hexane wash and hi-vac again.
KBS22-1 C3 flush 15-09-22_1.zip
KBS22-1 C3 flush 15-09-22 processed.pdf
Spectrum looks very promising otherwise - almost perfect match to MestreNova predictions.
from usyd_phd_eln.
26.09.22
Attempted ether wash but ether dissolved product - removed by rotary evaporation and put on hi vac overnight. This time, upon being put on hi vac, the product foamed up pleasingly.
Empty vial: 15.7096
Full vial: need to measure
from usyd_phd_eln.
IR
KBS22-1 04-11-22.pdf
KBS22-1.zip
from usyd_phd_eln.
H and C NMR, 500 MHz
20221108_KBS22-1 real_2 (1).zip
20221108_KBS22-1 real_1 (1).zip
13C NMR (126 MHz, CDCl3) δ 79.59, 59.43, 43.00, 35.93, 29.46, 28.53, 26.59.
1H NMR (500 MHz, CDCl3) δ 7.43 - 7.57 (2H), 4.44 (4H), 3.21 (4H), 2.24 (6H), 2.20 (12H), 1.77 (unknown- 12H?), 1.48 (4H), 1.44 (18H), 1.22 (4H).
from usyd_phd_eln.
HRMS
Hi Res ESI OK [M+Na] found error = 1.19 ppm
20221111_Service_HiRes_ESI_000011_2.pdf
20221111_Service_HiRes_ESI_000011.pdf
from usyd_phd_eln.
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