Objective

To check the stability of the furan ring of the Ugi adduct from benzaldehyde, 5-(Trifluoromethyl)-2-furylmethylamine , benzylisocyanide and Boc-Gly-OH (109C) in TFA to investigate the behavior of furan containing Ugi products.

Procedure

A solution of the Ugi product (54.5mg, 0.1mmol) (109C) and pure TFA (1mL) in a round bottom flask, with a condenser was heated for about 30 min under N2.

Results


109C HNMR
127A (Ugi+ TFA 30min reflux)
t = 4days
127B (after 2hr reflux)



Discussion


Conclusion


Log

2007-08-20

17:15 Set up reflux, added TFA (1000uL), Ugi product (54.5mg) and stirrer
17:20 Started heating, 2 bubbles/sec of nitrogen
17:22 Reflux began - 1 drop/sec
18:00 Took off heat
18:30 Obtained NMR of 127A. The solution was left at room temperature (exposed to air)

2007-08-24

15:51 Obtained HNMR of 127A (4days)
17:10 Ran nitrogen through experimental setup
17:12 Began heating solution
17:22 Started to reflux at 1 drop/sec
17:24 Solution began refluxing at 2 drops/sec
17:35 Solution refluxing at 3-4 drops/sec, turned down heat
17:40 Solution reluxing at 1-2 drops/sec
19:15 Took solution off of heat
19:35 Obtained HNMR of 127B in CDCl3