Comments (6)
25.07.22
- Added NaH (210 mg, 8.75 mmol) to a dry flask under nitrogen
- Added mono-propargyl 1,6-diaminohexane (SP of KBS17, 175 mg, 0.494 mmol) by solution transfer (dry DMF, 8 mL)
- Added 0.06 mL propargyl bromide (0.633 mmol, 1.3 equiv.)
- Left stirring from 4 pm
from usyd_phd_eln.
26.07.22
Reaction had turned black overnight.
from usyd_phd_eln.
28.07.22
- Diluted reaction with NH4Cl (10 mL) and water (40 mL).
- Extracted with toluene (4 x 25 mL)
- Washed with H2O (5 x 75 mL)
- Washed with brine (100 mL)
- Dried over MgSO4 and rotovapped
NMR
Product appears to still be a combination of mono/bis propargylated hexadiamine. Probably need to column manually to determine percentage yield.
from usyd_phd_eln.
29/07/22
Peaks at both 377.24 [M+Na] (mono product) and 415.26 [M+Na] (bis product).
KBS17-5 cr.d.zip
KBS17-5 cr.pdf
from usyd_phd_eln.
03.08.22
Performed a manual column to isolate mono and bis products. Used ~ 10 cm silica (possibly too much) and accidentally disturbed column bed part of the way through, possibly disrupting flow.
Column conditions:
50 mL 5:95 EtOAc/pet benzine
75 mL 6.7:93.3 EtOAc/pet benzine
100 mL 10:90 EtOAc/pet benzine
200 mL 20:80 EtOAc/pet benzine
50 mL 30:70 EtOAc/pet benzine
TLC's indicated bis product in fractions 18, 19, 20 and 22, 23, 24. Mono product appeared to be in fractions 26 - 35 but some SM was evident from fraction 29 onwards.
Note that M and D refer to references standards of mono-substituted and double-substituted products respectively, obtained from Nick Smith
from usyd_phd_eln.
03.08.22
Collected fractions 18 - 20 and 22 - 24 (believed to be bis product).
Empty vial: 16.1803
Full vial: 16.2002 g
Mass: 19.9 mg
H NMR
1H NMR (300 MHz, CDCl3) δ 4.02 (4H), 3.30 (4H), 2.18 (2H), 1.54 (4H), 1.47 (18H), 1.31 (4H).
Mysterious peak at 9.16 - seems like solvent (clean singlet, integrates to 0.43). There also appears to be water in the sample resulting in an increased integral at 1.54 (should be 4H but shows up as ~ 7H).
During the column, very faint signs of product could be seen in some fractions before F18. These weren't collected as the signal was so faint, however, collecting them may increase yield.
from usyd_phd_eln.
Related Issues (20)
- KBS43-3 - Nosyl protection of 1,6-diaminohexane HOT 4
- KBS48-1 - Mitsunobu reaction with KBS28 and KBS43 HOT 7
- KBS23-8 - Azidation of 1-naphthylamine HOT 2
- KBS28-9 - Click coupling of 1-azidonaphthalene and propargyl alcohol HOT 6
- KBS49-1 - Mitsunobu reaction with KBS28 and KBS45 HOT 9
- KBS49-2 - Mitsunobu reaction with KBS28 and KBS45 HOT 17
- KBS48-2 - Mitsunobu reaction with KBS28 and KBS43 HOT 15
- 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
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