newstrategy.JPG

Objective

To obtain a Ugi adduct and cyclize it to a diketopiperazine.

Procedure

To a 100ml round bottom flask a preformed 36B, 358mg, 2.0 mmol (assuming pure) in 2ml of Methanol-1M) was added to Boc-Met-OH (498mg, 2.0mmol in 2ml Methanol-1M), and 2-morpholin ethyl isocyanide (210µl, 2.0 mmol in 2ml Methanol-1M). The mixture will be stirred for atleast 24 hours before evaporation and isolation of the ugi adduct if required.

Conclusion

Experiment aborted

Log

2006-10-20
Ugi Reaction
11. 14:00] 36B ( 358mg, 2.0 mmol in 2ml of Methanol-1M ) is added to Boc-Met-OH (498mg, 2.0mmol in 2ml Methanol-1M), and 2-morpholin ethyl isocyanide (210µl, 2.0 mmol in 2ml Methanol-1M) and started to stir.
12.14:30] The reaction changed color from yellow to orange.

2006-10-25

13. 15:30] Stirring was stopped and methanol was evaporated under a gentle flow of Nitrogen. A brown solid was obtained.

2006-10-27

14. 18:50] The product was further set under a high vac for 3 hours to obtain 36C (0.998 mg)

Tags

Phenylacetaldehyde, InChI=1/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2
Boc-Methionine InChI=1/C10H19NO4S/c1-10(2,3)15-9(14)11-7(8(12)13)5-6-16-4/h7H,5-6H2,1-4H3,(H,11,14)(H,12,13)
tert -butylamineInChI=1/C4H11N/c1-4(2,3)5/h5H2,1-3H3
2-morpholin ethyl isocyanideInChI=1/C7H12N2O/c1-8-2-3-9-4-6-10-7-5-9/h2-7H2
ugi032: InChI=1/C29H48N4O5S/c1-28(2,3)33(26(35)23(13-20-39-7)31-27(36)38-29(4,5)6)24(21-22-11-9-8-10-12-22)25(34)30-14-15-32-16-18-37-19-17-32/h8-12,23-24H,13-21H2,1-7H3,(H,30,34)(H,31,36)