Exp095

= = = = == =Objective= To monitor the synthesis of a Ugi adduct from [|3,4-dimethoxybenzaldehyde], [|Furfurylamine], [|tert-butyl isocyanide] and [|Boc-Gly-OH] in methanol. =Procedure= Dissolved [|3,4-dimethoxybenzaldehyde] (Veratradlehyde) (83 mg, 0.5 mmol) and [|Furfurylamine](FFA) (58.7 uL, 0.55mmol, 10% excess ) in 1 mL methanol-d4 in a 1 mL volumetric flask, immediately transferred the contents to an NMR tube to monitor the imine formation reaction. Once the aldehyde peak disappeared a solution of [|Boc-Gly-OH](8[|t = 47min]7.5 mg, 0.5 mmol), and [|tert-butyl isocyanide](56.5 uL, 0.5 mmol) is made up in 1 ml volumeric flask in methanol-d4 is added to the preformed imine in the NMR tube. The reaction is monitored until a [|Ugi product] is obtained. =Results= (Reactant NMRs from Exp054) [|H NMR] (from EXP054 at about 1 M in methanol-d4) [|C NMR] [|H NMR] [| C NMR] [|H NMR] [|C NMR] [|H NMR] [|C NMR] [|t = 16min] [|t = 24min] [|t = 26min] [|t = 33min] [|t = 47min] [|t = 49min] [|t = 51min] [|t = 55min] [|t = 56min] [|t = 60min] [|t = 70min] [|t = 72min] [|t = 74min] [|t = 76min] [|t = 77min] [|t = 79min] [|t = 80min] [|t = 82min] [|t = 84min] [|t = 85min] [|t = 88min] [|t = 130min] [|t = 02min] [|t = 04min] [|t = 05min] [|t = 07min] [|t = 09min] [|t = 18min] [|t = 19min] [|t = 21min] [|t = 29min] [|t = 41min] =Discussion= =Conclusion= Experiment aborted. =Log=
 * Veratradehyde**
 * Furfurylamine**
 * //tert-B//utyl isocyanide**
 * Boc-Gly-OH**
 * 95A**
 * 95B**
 * 1) It is evident from the large amine to aldehyde ratio in the first 95A NMRs that an inaccurate amount of starting materials was used to perform the reaction. Based on the ratio of amine and imine peaks to the residual CHD2OD peak at 3.3 ppm (about 0.1 M based on several spectra, including the 1M veratraldehyde starting solution in EXP054), the starting aldehyde concentration is approximately 0.05 M, 10 times more dilute than expected. By similar analysis the starting amine concentration is correct, at about 0.5 M. This looks like a decimal place mistake on the scale.

2007-04-24
19:13 Madeup a solution of veratraldehyde and furfurylamine in 1ml methanol-d4 in a volumetric flask. This is **95A** 19:29 Obtained H NMR t = 16min 19:37 Obtained H NMR t = 24min 19:39 Obtained H NMR t = 26min 19:47 Obtained H NMR t = 33min 20:00 Obtained H NMR t = 47min 20:02 Obtained H NMR t = 49min 20:04 Obtained H NMR t = 51min 20:08 Obtained H NMR t = 55min 20:09 Obtained H NMR t = 56min 20:13 Obtained H NMR t = 60min 20:23 Obtained H NMR t = 70min 20:25 Obtained H NMR t = 72min 20:27 Obtained H NMR t = 74min 20:29 Obtained H NMR t = 76min 20:30 Obtained H NMR t = 77min 20:32 Obtained H NMR t = 79min 20:33 Obtained H NMR t = 80min 20:35 Obtained H NMR t = 82min 20:37 Obtained H NMR t = 84min 20:38 Obtained H NMR t = 85min 20:41 Obtained H NMR t = 88min 21:23 Obtained H NMR t = 130min 21:24 Added a solution of Boc Glycine and //tert//-Butylisocyanide in 1mL methanol-d4 to obtain **95B** 21:26 Obtained H NMR t = 02min 21:28 Obtained H NMR t = 04min 21:29 Obtained H NMR t = 05min 21:31 Obtained H NMR t = 07min 21:33 Obtained H NMR t = 09min 21:42 Obtained H NMR t = 18min 21:43 Obtained H NMR t = 19min 21:46 Obtained H NMR t = 21min 21:53 Obtained H NMR t = 29min 22:04 Obtained H NMR t = 41min

=Tags= [|3,4-dimethoxybenzaldehyde] I[|nChI=1/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3] [|Furfurylamine] [|InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2] [|tert-butyl isocyanide][|InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3] [|Boc-Gly-OH][|InChI=1/C7H13NO4/c1-7(2,3)12-6(11)8-4-5(9)10/h4H2,1-3H3,(H,8,11)(H,9,10)] [|Product][| InChI=1/C26H37N3O7/c1-25(2,3)28-23(31)22(17-11-12-19(33-7)20(14-17)34-8)29 (16-18-10-9-13-35-18)21(30)15-27-24(32)36-26(4,5)6/h9-14,22H,15-16H2,1-8H3,(H,27,32)(H,28,31)] media type="custom" key="51617"