Objective

To synthesize 5 Ugi products following the EXPLAN005 . The compound will contribute towards a library for Falcipain2 inhibitors.
These compunds were ranked 153-157 in the DEXP014-V1B file from D-EXP014.

Procedure

As described in Explan005
500 ul of methanol was used.

Comp ID/ Lib Rank
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
143a/153
Phenanthrene-9- carboxaldehyde
(0.25mmol, 45.05 ul)
n-heptylamine
(0.25mmol, 37.07 ul)
crotonic acid
(0.25 mmol, 21.52 mg)
tert-butylisocyanide
(0.25 mmol, 28.28 ul)
no
143b/154
benzaldehyde
(0.25mmol, 25.39ul)
methylamine
(0.25 mmol, 25.00 ul),
3-nitrobenzoic acid
(0.25mmol, 41.78 mg)
Tosylmethylisocyanide
(0.25mmol, 48.8mg)
no
143c/155
Phenanthrene-9- carboxaldehyde
(0.25mmol, 45.05 ul)
benzylamine
(0.25 mmol, 26.79 ul)
crotonic acid
(0.25 mmol, 21.52 mg)
tert-butylisocyanide
(0.25 mmol, 28.28 ul)
no
143d/156
o-tolualdehyde
(0.25 mmol, 30.04 ul)
propylamine
(0.25 mmol, 20.55 ul)
4-Chlorophenylacetic acid
(0.25 mmol, 42.65 mg)
Tosylmethylisocyanide
(0.25mmol, 48.8mg)
no
143e/157
2-methoxynaphthaldehyde
(0.25 mmol, 46.55 mg)
tert-butylamine
(0.25 mmol, 26.27 ul)
glycolic acid
0.25 mmol, 19.01 mg)
Tosylmethylisocyanide
(0.25mmol, 48.8mg)
yes

Results

Exp143compd153a-157a.JPG
Image of the five vials from the first day.


Exp143-2nd-day.JPG
Image of experiment 143 from the second day.

Discussion

All results are recorded in the Master Table of all Ugi synthesis attempts
Exp 143a and 143c required phenanthrene-9-carboxaldehyde. The compound that was used was a liquid, but it should have been a solid. HNMR spectra need to be taken for the existing liquid sample and the newly purchased sample from Sigma-Aldrich. From the image it does not look like there is a precipitate for 143e - if there was it should have been isolated by centrifuging.

Conclusion

The phenanthrene-9-carboxaldehyde batch was bad by NMR, and experiment 143a and 143c must be done again using the new compound.

Log

2007-11-7

18:40 Began to weight out crotonic acid for comp 143a.
18:55 Finished comp 143a and began to weigh out 3-nitrobenzoic acid and tosylmethylisocyanide for comp 143b.
19:12 Finished with comp 143b and began to weigh out crotonic acid for comp 143c.
19:25 Finished with comp 143c and began to weigh out tosylmethylisocyanide and 4-chlorophenylacetic acid for comp 143d.
19:40 Finished with comp 143d and began to weigh out 2-methoxynaphthaldehyde, glycolic acid and tosylmethylisocyanide for comp 143e.
19:55 Finished comp 143e and took a picture of the 5 vials.
no log of when second pic was taken

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