Comments (6)
29.11.22
- Added NaH (163.5 mg of 60% dispersion in mineral oil, 4.09 mmol, 2.90 equiv.) to a dry flask
- Washed with pet. benz. (3 x 5 mL)
- Added KBS3-3 (447.7 mg, 1.41 mmol) dissolved in dry DMF (10 mL)
- Left stirring at rt from 10.30 am
TLC indicated "activation step" (deprotonation by NaH) was complete at 1.45 pm.
Reaction at 1.45 pm
- Cooled to 0 C
- Added propargyl bromide (0.5 mL, 80% in toluene, 6.60 mmol, 4.7 equiv.)
Reaction went black instantly upon addition of propargyl bromide.
TLC at 4.45 pm indicated formation of mono and bis product already, but SM remained.
from usyd_phd_eln.
30.11.22
TLC at 9.30 am indicated formation of mono and bis products.
20% ethyl acetate/pet. benz.; from left to right: 17-10, 17-10/starting material co spot, starting material, 17-11/starting material cospot, 17-11
from usyd_phd_eln.
01.12.22
TLC at 10 am.
Decided to work up despite SM remaining (~ 48 hours reaction time).
- Quenched with NH4Cl (20 mL)
- Extracted with toluene (4 x 50 mL)
- Washed with water (5 x 100 mL)
- Washed with brine (125 mL)
- Dried over mag sulphate and rotovapped.
Reaction after quenching
Reaction after brine wash
Empty vial: 15.8697
Full vial: 16.3023
Mass: 432.6 mg
from usyd_phd_eln.
8.12.22
Column
Ethyl acetate/pet. benz.
100 mL - 5%
250 mL - 10%
200 mL - 20%
100 mL - 50%
100 mL - 100%
Label | Fractions | Vial weight (g) | Vial weight (full) | Mass (mg) | Moles (mmol) | Yield |
---|---|---|---|---|---|---|
B | 10-12 | 15.7548 | - | - | - | - |
C | 13-22 | 15.7553 | 15.8522 | 96.9 | 0.247 | 18% |
D | 23-24 | 15.4883 | 15.5064 | 18.1 | 0.046 | 3% |
E | 25-29 | 15.5235 | 15.6196 | 96.1 | 0.271 | 19% |
F | 30-34 | 15.9494 | 15.9747 | 25.3 | 0.071 | 5% |
G | 35+ |
from usyd_phd_eln.
07.12.22
Column TLCs.
from usyd_phd_eln.
20.12.22
LRMS
KBS-17-10_2-A,6_1_693-1.pdf
KBS-17-10_2-A,6_1_693.pdf
Evidence of mono product (377.26) and bis product (415.29) in a ratio of roughly 77:100 i.e. mono = 44%, bis = 56%.
from usyd_phd_eln.
Related Issues (20)
- KBS50-1 - Nosyl protection of bis(3-aminopropyl)amine HOT 13
- KBS44-2 - Nosyl deprotection of KBS49 HOT 10
- KBS50-2 - Nosyl protection of bis(3-aminopropyl)amine HOT 9
- KBS53-1 - Nosyl deprotection of KBS48 HOT 12
- 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 9
- 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 4
- 2023_BG_12C
- more samples
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