Researcher

David Bulger

Objective

To synthesis four Ugi products in eight solvent at three concentrations.

Procedure

Ugi Product
Aldehyde
Primary Amine
Carboxylic Acid
Isocyanide
Known (**tert-butyl (2-{[2-(tert-butylamino)-2-oxo-1-phenylethyl](furan-2-ylmethyl)amino}-2-oxoethyl)carbamate**)
benzaldehyde
furfurylamine
boc-glycine
t-butylisocyanide
230-1
benzaldehyde
furfurylamine
boc-glycine
cyclohexylisocyanide
230-2
p-tolualdehyde
hexylamine
boc-glycine
t-butylisocyanide
230-3
p-tolualdehyde
hexylamine
boc-glycine
cyclohexylisocyanide
Using 96 well container as follows:
Wells
1 (Known at 0.25M)
2 (Known at 0.50M)
3 (Known at 1.00M)
4 (230-1 at 0.25M)
5 (230-1 at 0.50M)
6 (230-1 at 0.75M)
7 (230-2 at 0.25M)
8 (230-2 at 0.50M)
9 (230-2 at 1.00M)
10 (230-3 at 0.25M)
11 (230-3 at 0.50M)
12 (230-3 at 1.00M)
A - Ethanol












B - Methanol












C - THF












D - DMSO












E - DMF












F - Acetonitrile












G - Isopropanol












H - Chloroform












Results

Pictures

UC230-1
UC230-2
UC230-3
UC230-4
UC230-5
UC230-6

Spreadsheet

UC230-1 (General Spreadsheet with Calculations)[note the wells only hold 300 microliters JCB]

Conclusion

[As we discussed we learned some important things from this experiment - note them here JCB]
[Most importantly it was not possible to properly seal the wells with the lid provided for aqueous experiments and solvents evaporated quickly. Also it was difficult to see which wells held precipitates. JCB]

Improper sealing of the wells in this experiment allowed some problems to arise. As some of the solutions were volatile, the pressure unsealed the para-film covering allowing the solution to condense on the underside of the para-film. Once on the para-film, the solution appeared to travel across to the other wells tainting them. This resulted in the mixing of most of the solutions. In addition, some of the solutions such as chloroform dissolved the para-film. Furthermore, the amount of solution added to the wells exceeded the amount the wells could hold without overflowing. Overall, precipitation could not be distinguished from starting materials and the reaction mixtures contained large amounts of impurities.

Log

2009-05-26
18:46 Weighed 1-dram vials:
Vial
Mass (g)
AS
5.101 5
BS
5.079 6
CS
5.130 2
DS
5.124 3
ES
5.112 0
FS
5.063 8
GS
5.103 8
HS
5.075 9
18:57 Added 0.219 0 g of boc-Glycine to each vial and weighed
Vial
Mass (g)
AS
5.320 5
BS
5.298 7
CS
5.349 0
DS
5.342 9
ES
5.331 5
FS
5.283 6
GS
5.322 8
HS
5.294 9
19:40 Added 436 uL of solvent to vials
Vial
Solvent
AS
Ethanol
BS
Methanol
CS
THF
DS
DMSO
ES
DMF
FS
Acetonitrile
GS
Isopropanol
HS
Chloroform
19:54 Vortexed each for 30 sec
20:00 Photo (UC230-1)
20:01 Added 10.2 uL of benzaldehyde to wells (A-H)1-6 while parafilming following the addition to each row of wells
20:15 Added 11.8 uL of p-tolualdehyde to wells (A-H)7-12 while parafilming following the addition to each row of wells
20:25 Added 8.8 uL of furfurylamine to wells (A-H)1-6 while parafilming following the addition to each row of wells
20:40 Added 13.2 uL of hexylamine to wells (A-H)7-12 while parafilming following the addition to each row of wells
20:53 Photos (UC230-2, UC230-3) - Note: Solvent seems to be evaporating from wells and parafilm doesn't seem to seal the wells very tightly
20:54 Added 50.0 uL of boc-Glycine solutions (AS-HS) as follows while parafilming following the addition to each row of wells:
Wells
Solution
A1-A12
AS (ethanol)
B1-B12
BS (methanol)
C1-C12
CS (THF)
D1-D12
DS (DMSO)
E1-E12
ES (DMF)
F1-F12
FS (Acetonitrile)
G1-G12
GS (Isopropanol)
H1-H12
HS (Chloroform)
21:20 Photos (UC230-4, UC230-5) - Note: Solvent seems non-existant in some vials (only solid remaining) - evaporated solvent seems to be traveling along parafilm into some of the other wells (previously white wells on the right half becoming tainted yellow by the evaporation yellow solutino from the left wells)
21:21 Added 11.3 uL t-butyl isocyanide to (A-H)1-3 and (A-H)7-9 and added 12.4 uL cyclohexylisocyanide to (A-H)4-6 and (A-H)10-12 while parafilming following the addition to each row of wells
21:45 Added solvent to each of the wells as follows while parafilming following the addition to each row of wells:
Wells
1
2
3
4
5
6
7
8
9
10
11
12)
A - Ethanol
320 uL - this column overflowed the wells
120 uL
19.7 uL
Column 1 vials overflowed with solvent -
therefore Columns 4,7 and 10 aborted
119 uL
19 uL
Aborted
114 uL
14 uL
Aborted
113 uL
12.6 uL
B - Methanol
320 uL
120 uL
19.7 uL
Aborted
119 uL
19 uL
Aborted
114 uL
14 uL
Aborted
113 uL
12.6 uL
C - THF
320 uL
120 uL
19.7 uL
Aborted
119 uL
19 uL
Aborted
114 uL
14 uL
Aborted
113 uL
12.6 uL
D - DMSO
320 uL
120 uL
19.7 uL
Aborted
119 uL
19 uL
Aborted
114 uL
14 uL
Aborted
113 uL
12.6 uL
E - DMF
320 uL
120 uL
19.7 uL
Aborted
119 uL
19 uL
Aborted
114 uL
14 uL
Aborted
113 uL
12.6 uL
F - Acetonitrile
320 uL
120 uL
19.7 uL
Aborted
119 uL
19 uL
Aborted
114 uL
14 uL
Aborted
113 uL
12.6 uL
G - Isopropanol
320 uL
120 uL
19.7 uL
Aborted
119 uL
19 uL
Aborted
114 uL
14 uL
Aborted
113 uL
12.6 uL
H - Chloroform
320 uL
120 uL
19.7 uL
Aborted
119 uL
19 uL
Aborted
114 uL
14 uL
Aborted
113 uL
12.6 uL
22:09 Photo (UC230-6) and let sit with book on top of parafilmed wells