Comments (6)
03.11.22
- Added NaH (175.3 mg, 4.38 mmol, 3.5 equiv.) to a oven dry flask under nitrogen
- Washed mineral oil off with pet. benz. (3 x 5 mL)
- Added KBS3 (397.8 mg, 1.26 mmol) dissolved in DMF dried over sieves (10 mL)
- left stirring at rt for 1 hr 45 mins
TLC indicated deprotonation step was not complete
Checked again after 2.5 hours. TLC indicated deprotonation was more progressed.
- Cooled to 0 C
- Added dropwise propargyl bromide (0.5 mL, 4.67 mmol, 3.7 equiv.) that had been freshly passed through aluminum to remove impurities (e.g. HBr)
- Left to warm to rt in ice bath overnight
from usyd_phd_eln.
07.11.22
INSERT TLC
- Quenched with 20 mL NH4Cl (10-15 minutes stirring)
- Extracted with toluene (5 x 25 mL) and washed with water (5 x 50 mL)
- Washed with brine (100 mL) and dried over mag sulphate
- Filtered and rotovapped
Empty vial: 15.6536
Full vial: 16.0547
Mass: 401.1
H NMR
KBS17-9_1.zip
KBS17-9 cr processed.pdf
Evidence of both mono and bis products.
LCMS/MS
KBS-17-9_1-D_5_1_392.d.zip
KBS-17-9_1-D_5_1_392__Generic_Display_Report.pdf
KBS-17-9_1-D_5_1_392_Compound_Spectrum_List_Report.pdf
from usyd_phd_eln.
15.11.22 - columning crude product
10 cm silica
Ran ~ 200 mL of 5% ethyl acetate before disturbing column bed irreparably. Salvaged as much crude product as possible.
Salvaged product = 379.5 mg
Note that column numbering was continued across the two columns i.e. fraction 10 is the last collected before the column was ruined and fraction 11 is the first collected from the fresh column.
Second column
-
200 mL 5% ethyl acetate in petroleum benzine
-
250 mL 10%
-
200 mL 20%
-
50 mL 30%
-
200 mL 100%
from usyd_phd_eln.
16.11.22 - Results of column
Compound | Fractions | Tare weight | Final weight | Mass | Percentage yield (see notes) |
---|---|---|---|---|---|
Bis | 39-44 | 15.7929 | 15.8686 | 75.7 mg (0.192 mmol) | 15% |
Bis/mono | 45-46 | 15.7705 | 15.7783 | 17.8 mg (0.045 mmol) | 4% |
Mono | 47-51 | 15.7911 | 15.9331 | 142 mg (0.400 mmol) | 32% |
Mono/SM | 52-54 | 15.8134 | 15.8173 | 4 mg (0.00113 mmol) | < 1% |
SM | 55+ | 15.8383 | 15.9395 | 101.2 mg, 0.320 mmol) | 25% |
H NMR
KBS17-9 F39-44_1.zip - bis product
KBS17-9 45-46_1.zip - mixed bis/mono
KBS17-9 F47-51_1.zip - mono product
KBS17-9 55+_1.zip - starting material
from usyd_phd_eln.
21.11.22
LRMS
KBS17-9 39-44.pdf
Bis product - 415.26 [M+Na]+
KBS17-9 47-51.pdf
Mono product - 377.23 [M+Na]+
KBS17-9 55+.pdf
SM - 339.23 [M+Na]+
from usyd_phd_eln.
22.11.22
Decided to run 20% MeOH in DCM through column to get rid of last band - see image.
from usyd_phd_eln.
Related Issues (20)
- KBS44, 52, 53 (Nosyl deprotection) - master page HOT 4
- KBS50-1 - Nosyl protection of bis(3-aminopropyl)amine HOT 13
- KBS44-2 - Nosyl deprotection of KBS49 HOT 11
- KBS50-2 - Nosyl protection of bis(3-aminopropyl)amine HOT 9
- KBS53-1 - Nosyl deprotection of KBS48 HOT 13
- KBS52-1 - Nosyl deprotection of KBS51 HOT 7
- KBS51-1 - Mitsunobu reaction with KBS28 and KBS50 HOT 10
- KBS53-2 - Nosyl deprotection of KBS48 HOT 10
- KBS48 (pooled) - purification HOT 3
- KBS52-2 - Nosyl deprotection of KBS51 HOT 2
- KBS51-2 - Mitsunobu reaction with KBS28 and KBS50 HOT 5
- KBS22-2 - Linear click coupling of bis-propargyl diaminohexane and azidoadamantane HOT 6
- Carlota's compounds - for purification HOT 2
- KBS22-3 - Linear click coupling of bis-propargyl diaminohexane and azidoadamantane HOT 8
- KBS52-3 - Nosyl deprotection of KBS51 HOT 15
- 2024_BG_A_1 - Formation of benzoyl thioureas HOT 2
- 2024_BG_B_1 - Hydrolysis of benzoyl thioureas HOT 2
- SAR - for future aminothiazoles
- 2024_BG_C - characterisation of final compounds HOT 5
- 2023_BG_12C
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