exp079

== =Objective= To cyclize a [|Ugi product] to form a [|diketopiperazine] via a [|boc-deprotected intermediate]. This [|Ugi product] was synthesized here.

= = =Procedure= Prepared 10% TFA solution by adding 80uL TFA to 1 dram vial. Added 720uL1,2 dichloroethane. Took NMR spectra. Added 50mg Ugi Product ([|62E]) to NMR tube and monitored reaction via NMR spectra at specific intervals.

=Results= 10% TFA Solution [|HNMR]

62E [|HNMR]

Ugi/TFA before reflux (T=50 mins) [|HNMR]

T=24hrs [|HNMR]

=Discussion= 1. The de-protection is evident with the appearance of a singlet peak at 1.6ppm (corresponding to t-butyl trifluoroacetate) after 50 mins. 2. After twenty four hours the Ugi product is completely de protected, although this is somewhat unreliable because the reaction evaporated. =Conclusion= The Ugi product was deprotected however the product did not cyclize.

=Log=

2007-03-28
11:17 Set temperature bath to 80C. Prepared 10% TFA solution. 11:46 Added 400uL TFA solution to NMR tube. Added 400uLdeuterated chloroform to NMR tube. Took NMR spectra.(solution slight yellow) 12:38 Unable to get spectra until 12:30. Weighed out 50mg of 62E. Added to contents of NMR tube. (solution orange-red) 12:46 Took NMR spectra. 13:43 Unable to get spectra until 13:35. Temperature bath at 81C. Placed NMR tube in temperature bath. Solution turned red. 13:57 Noticed condensation in NMR tube. Temperature bath 81C. 14:30 Contents in NMR tube evaporated. Removed from heat. 16:12 Added 500uL deuterated chloroform to NMR tube.

2007-03-29
13:10 Took NMR spectra.

=Tags= [|Ugiproduct][|InChI=1/C26H35N3O7/c1-16-8-10-18(35-16)14-29(21(30)13-27-24(32)36-26(5,6)7)22(23(31)28-25(2,3)4)17-9-11-19-20(12-17)34-15-33-19/h8-12,22H,13-15H2,1-7H3,(H,27,32)(H,28,31)] (**//why are there extra characters not in the URL//**?) [|DKP065] [|InChI=1/C17H16N2O5/c1-10-2-4-12(24-10)8-19-15(20)7-18-17(21)16(19)11-3-5-13-14(6-11)23-9-22-13/h2-6,16H,7-9H2,1H3,(H,18,21)]