Comments (8)
##28.06.22
- KBS3 (410 mg, 1.30 mmol) was dissolved in dry DMF (15 mL) and added to a dry flask containing NaH (445 mg, 11.1 mmol, 60% mineral oil dispersion, 8.6 equiv.) under nitrogen
- Propargyl bromide (0.51 mL, 4.55 mmol, 80% in toluene, 3.5 equiv.) was added
- The mixture was stirred at room temperature from 11 am. It went a black colour (from a straw-yellow colour) shortly after the propargyl bromide was added
- TLC at 3.30 pm indicated reaction was proceeding but not yet complete
from usyd_phd_eln.
29.06.22
- TLC at 10 am indicated the reaction was complete
- Quenched with NH4Cl (sat., 25 mL)
- Extracted with diethyl ether (4 x 40 mL). Lots of black emulsion made separation more difficult. Both aqueous layer and combined organic extracts were a red-orange colour.
- Brine wash (115 mL)
- Dried over MgSO4 and rotovapped down
Vial (empty) = 15.7175
Vial (full) = 16.3033
Mass = 585.8 mg
NMR
1H NMR (300 MHz, Chloroform-d) δ 4.02 (s, 4H), 3.30 (s, 4H), 2.17 (s, 2H), 1.58 (s, 4H), 1.45 (d, J = 7.2 Hz, 18H), 1.26 (s, 4H).
KBS17-3 cr_1.zip
KBS17-3 cr processed.pdf
All expected peaks are present but integrals are too large for results < 2 ppm. Potentially due to having 2 products (mono and bis) which have minimally different peaks in this zone - need to figure out what the mono product is expected to look like.
from usyd_phd_eln.
30.06.22
Decided to try and figure out what might be in the aqueous layer, as it was strongly coloured (reddish brown). pH was neutral (see image), so added NaOH (2.5 M) until it reached pH 11/12 (as tested by universal indicator strips) - wouldn't go higher even with addition of copious amounts of NaOH.
Extracted with ethyl acetate (2 x 80 mL) and got a straw-coloured organic extract. Dried over MgSO4 and rotovapped down.
First extraction with ethyl acetate
from usyd_phd_eln.
LRMS
KBS17-3.pdf
20220701_KBS17-3c.d.zip
from usyd_phd_eln.
15.07.22
Tried and failed to rotovap down second extraction so dissolved in toluene (~ 5 mL) and washed with water (5 x 10 mL).
Vial (empty): 15.7032 g
Vial (full): 15.7215 g
Mass: 18.3 mg
NMR
Initial NMR analysis (1H NMR, 300 MHz) indicates that coloured substance is product rather than starting material.
KBS17-3 SP_1.zip
KBS17-3 SP processed.pdf
from usyd_phd_eln.
20.07.22
Columned crude product with upsetting results. First column produced 4 separate spots on TLC, each of which were collected separately.
A - F 1-5 - 88 mg
B - F 6-9 - 34 mg
C - F 10-12 - 3 mg
D - F >13 - 12 mg
However, as the mass total was significantly less than the ~ 500 mg crude product, the column was washed again with another gradient. All fractions showing signs of product of any kind were collected as one "runoff" sample.
Runoff = 176 mg
NMR analysis of the samples indicated that A contained only solvent and nothing of interest. B contained something, but had no tell-tale Boc peak at 1.45 so didn't appear to be either SM or product. C was not analysed as there was too little. D contained a very small amount of material which appeared to be the same as the product seen in the Runoff sample - this material had a Boc peak and was not SM.
The Runoff sample was then analysed via mass spec. This indicated the presence of the mono-propargylated product (377.24, [M+Na]) with only a tiny peak indicating that the bis-propargylated product might be present (393.23, [M+H]).
NMR
1H NMR (300 MHz, CDCl3) δ 4.53, 4.01, 3.29, 3.13, 3.09, 2.18, 1.46, 1.43, 1.21.
LRMS
F3-8
Empty vial: 15.7611
Full vial: 15.7960
Mass: 34.9 mg
F9-24
Empty vial: 15.8789
Full vial: 15.8911
Mass: 12.2 mg
from usyd_phd_eln.
20.07.22
Ran off remainder of column (30 -100% ethyl acetate in hexane over 12 CV).
F3-8
Empty vial: 15.7611
Full vial: 15.7960
Mass: 34.9 mg
F9-24
Empty vial: 15.8789
Full vial: 15.8911
Mass: 12.2 mg
from usyd_phd_eln.
25.07.22
Ultimately only one product was isolated. This was identified as the mono-propargylated side product rather than the bis-propargylated product. It was recovered in a yield of 38% (175 mg, 0.494 mmol).
This side product was carried on into #23.
from usyd_phd_eln.
Related Issues (20)
- MTS 2 - MIC and High/Low for MycetOS compounds (duplicate) HOT 6
- KBS17 - master page HOT 1
- VIV2 - MycetOS compounds HOT 1
- TOX1 - MYOS423, 726, 727, 731 HOT 1
- MTS-3 - USYD compounds (triplicate) and York compounds (initial) HOT 7
- TOX-2 - MYOS432, 617 and 619 HOT 1
- TOX-3 - MYOS compounds 423, 432, 617, 619, 726, 727, 731 (duplicate) HOT 1
- VIV-3 - MYOS423, 617, 619. 727 and 731 HOT 4
- MTS-4 - USyd compounds (if needed), York compounds (duplicate) HOT 7
- VIV-5 - MYOS compounds duplicate HOT 1
- VIV-6 - MYOS423, 619, 727, 731 HOT 1
- TOX-4 - Duplicate for compounds 423, 726, 727, 731 HOT 1
- MTS-5 - USyd + U of York + UCL compounds HOT 4
- VIV-7
- VIV-4 - MYOS compounds 423, 617, 619, 727 HOT 1
- MTS-6 - USyd + U of York + UCL compounds HOT 1
- TOX-5 - replicate for 423, 726, 727, 731 HOT 1
- VIV-8
- MTS-7 - USyd repeats + Uni of York / UCL high-low replicates + Uni of York MIC replicates
- TOX-6 - triplicates for USyd compounds MYOS423, 432, 617, 619, 726, 727, 731
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