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12th December 2014 @ 04:32
AEW 211-1 (80 mg, 0.17 mmol, 1 equiv) was dissolved in anhydrous CH2Cl2 (0.5 mL) and TFA (0.5 mL) was added and the reaction mixture was stirred for 30 mins. Still SM monitored over next 2 hours. TLC shows spot at same Rf as SM in the product but not as bright in UV. Stirred for a further 30 mins. Excess reagent and solvent were removed under vacuum. The resulting red oil was neutralisedd by 2NKOH (4 mL) extracted with DCM (5× 5 mL), dried over MgSO4, filtered and evaporated to give an orange/brown oil that was purified using the Isolera. 10 g column, repacked and product adsorbed onto silica and dry loaded. (DCM/MeOH gradient see: attached PDF).  Detector failed and fraction 3 was not collected (should be according to UV trace) so collect all was started. Two distinct spots Frac A contained in tube 4 was highly UV visible top spot (10 mg brown oil) and Frac A lower spot thought to be product (10 mg). Both dissolved in CDCl3 for NMR evaluation.   Data:  TLC 9:1 DCM/MeOH [data]14315[/data][data]14317[/data]   2.5 h [data]14353[/data] Isolera Reports: [data]14357[/data][data]14355[/data] Hazard and Risk Assessment: Literature Reference: http://pubs.acs.org/doi/pdf/10.1021/ol048771l Highly Efficient Stereoconservative Amidation and Deamidation of alpha-Amino AcidsDeepak M. Shendage, Roland Fröhlich, and Günter Haufe Org. Lett., Vol. 6, No. 21, 2004, 3675-3678 Strings: InChI=1S/C25H26FN5O4/c1-25(2,3)35-24(32)28-20(17-7-5-4-6-8-17)15-33-22-14-27-13-21-29-30-23(31(21)22)18-9-11-19(12-10-18)34-16-26/h4-14,20H,15-16H2,1-3H3,(H,28,32) to InChI=1S/C20H18FN5O2/c21-13-28-16-8-6-15(7-9-16)20-25-24-18-10-23-11-19(26(18)20)27-12-17(22)14-4-2-1-3-5-14/h1-11,17H,12-13,22H2/t17-/m0/s1 FCOC(C=C1)=CC=C1C2=NN=C3C=NC=C(OC[C@H](NC(OC(C)(C)C)=O)C4=CC=CC=C4)N32 to N[C@H](C1=CC=CC=C1)COC2=CN=CC3=NN=C(C4=CC=C(OCF)C=C4)N32
Attached Files
AEW 213-1.cdxml
AEW 213-1.png
AEW 213-1 (DCM:MeOH 9:1).jpg
AEW 213-1 (DCM:MeOH 9:1, 9h ruler view).jpg
AEW 213-1 TLC (9:1 DCM:MeOH).jpg
aew 213-1_frac.pdf
aew 213-1_arch.pdf