Exp121

= = == =Objective= To synthesize a Ugi adduct from //o//-Vanillin, 5methyl furfurylamine Boc-tryptophan and 1-pentylisocyanide. =Procedure= A solution of //o//-Vanillin (76.05mg, 0.5 mmol) and 5-methylfurfurylamine (55.7uL, 0.5 mmol) was prepared in methanol-d4 in an 1ml volumetric flask to form an imine. Then Boc-Tryptophan (152.17mg, 0.5mmol), and 1-pentylisocyanide (62.9uL 0.5 mmol) was added to the preformed imine. The crystalline product was centrifuged, washed and recrystallized from methanol (5mL). =Results= [| HNMR] [| CNMR] [|H NMR] [|C NMR] [| HNMR] [| CNMR] [| HNMR] [| CNMR] [|HNMR] [| CNMR] [|09min] [|24min] [|31min] [|41min] [|1h 2min] [|1h 33min] [|16min] [|17h 52min]
 * Characterization of 121ugi**
 * //o//-Vanillin**
 * 5-methylfurfurylamine**
 * Boc-Tryptophan**
 * 1-pentylisocyanide**
 * 1-Butylisocyanide**
 * 121A**
 * 121B**

=Conclusion= No Ugi product isolated =Log=

2007-08-15
17:19 Madeup a solution of o-vanillin and 5-methyl furfurylamine in CD3OD in a 1ml volumetric flask, transferred to an NMR tube to form 121 A 17:28 Obtained HNMRs of 121A (09min) 17:45 Obtained HNMRs of 121A (24min) 17:50 Obtained HNMRs of 121A (31min) 18:00 Obtained HNMRs of 121A (41min) 18:21 Obtained HNMRs of 121A (1h 2min) 18:52 Obtained HNMRs of 121A (1h 33min) 19:10 Completed the addition of boc-tryptophan and pentyl isocyanide to give 121B 19:26 Obtained HNMR of 121B (16min)

2007-08-16
10:00 Solid has appeared in the solution of 121B 14:02 The solution in the NMR tube was shaken vigorously, the solid which had appeared dissolved...thereby allowing an HNMR tobe taken. (17h 52)

2007-08-17
10:00 Although there is some solid visible in the tube, but it may not isolable because of its mere quantity. =Tags= [|o-vanillin] [|InChI=1/C5H11NS2.Na/c1-3-6(4-2)5(7)8;/h3-4H2,1-2H3,(H,7,8);/q;+1/p-1/fC5H10NS2.Na/q-1;m] [|5-methyl-furfurylamine] [|InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3] [|Boc-trp-OH] [|InChI=1/C16H20N2O4/c1-16(2,3)22-15(21)18-13(14(19)20)8-10-9-17-12-7-5-4-6-11(10)12/h4-7,9,13,17H,8H2,1-3H3,(H,18,21)(H,19,20)] [|n-butylisocyanide] [|InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3] [|n-pentylisocyanide] [|InChI=1/C6H11N/c1-3-4-5-6-7-2/h3-6H2,1H3]