Ct. The solution can’t be simply converted to any recognized structure.
Ct. The solution can’t be conveniently converted to any recognized structure.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTypical Process for the -Amination of your AldehydeA modification of reported procedure38 was made use of. Dibenzyl azodicarboxylate (90 , 1.29 g, 3.9 mmol) and proline (70 mg, 0.6 mmol) in MeCN (ten mL) have been cooled down to -3 . The aldehyde (1.02 g three.0 mmol) was then added and the mixture was stirred at -3 for 2 h. The reaction was steadily warmed to 20 inside ca. 1 h. The mixture was then cooled to 0 , treated with MeOH (three mL) and NaBH4 (240 mg, six.0 mmol) and was stirred for five min at 0 . The reaction was quenched by 1M KHSO4. The aqueous solution was extracted with EtOAc three times. The combined organic layers have been dried with MgSO4, and concentrated in vacuo. Purification on the residue by flash chromatography on silica gel, eluting with 15 EtOAchexanes gave the preferred alcohol as white foamy strong.J Org Chem. Author manuscript; offered in PMC 2014 December 06.Khumsubdee et al.PageNIH-PA Author ManuscriptDibenzyl 1-((2R,3S)-4-((tert-Butyldiphenylsilyl)oxy)-1-hydroxy-3-methylbutan-2yl)hydrazine-1,2-dicarboxylate (anti-9) The compound was prepared in accordance with the c-Rel Source common -amination process catalysed by (R)-Proline. Purification by flash chromatography afforded MDM2 Formulation anti-9 as a white foamy solid (1.54 g, 80 isolated yield). 1H NMR (400 MHz, CDCl3) 7.70 7.67 (m, 4H), 7.50 7.27 (m, 16H), 6.85 (d, J = 31.1 Hz, 1H), five.37 five.ten (m, 4H), 4.45 four.12 (m, 2H), three.80 3.41 (m, 4H), 1.95 1.66 (m, 1H), 1.12 1.09 (m, 9H), 0.99 0.88 (m, 3H); 13C NMR (100 MHz, CDCl3) 159.1, 157.four, 135.6, 133.three, 133.two, 129.six, 129.eight, 128.7, 128.six, 128.two, 127.9, 127.eight, 127.7, 68.62, 65.88, 65.56, 60.37, 35.6, 26.9, 19.3, 15.1. IR (CH2Cl2) n (cm-1) 3356, 3032, 2928, 1717, 1454, 1408, 1265, 1227, 1111, 1057. HRMS (ESI, TOF): mz = 641.3078, calcd For C37H45N2O6Si [MH] 641.3047. The diastereoselectivity was 1.0:13, determined by Chiral HPLC (Chiralcel OD, HexiPrOH 93:7, 1 mLmin, 25 ), tr ten.3 min (minor diastereomer), tr 14.4 min (important diastereomer).NIH-PA Author Manuscript NIH-PA Author ManuscriptDibenzyl 1-((2S,3S)-4-((tert-Butyldiphenylsilyl)oxy)-1-hydroxy-3-methylbutan-2yl)hydrazine-1,2-dicarboxylate (syn-9) The compound was prepared as outlined by the typical -amidation process catalysed by (S)-Proline. Purification by flash chromatography afforded syn-9 as a white foamy strong (1.63 g, 85 isolated yield). 1H NMR (400 MHz, CDCl3) 7.69 7.62 (m, J = 13.five, six.6 Hz, 4H), 7.50 7.24 (m, 16H), six.96 (s, 1H), five.30 5.22 (m, 3H), five.13 (dd, J = 12.1, 9.6 Hz, 1H), 4.36 4.16 (m, 2H), 3.86 three.70 (m, 2H), three.59 3.44 (m, 2H), 1.80 (br, 1H), 1.11 1.08 (m, 9H), 0.93 0.90 (m, 3H); 13C NMR (100 MHz, CDCl3) 158.6, 158.two, 156.8,J Org Chem. Author manuscript; available in PMC 2014 December 06.Khumsubdee et al.Page156.5, 135.9, 135.six, 135.5, 135.4, 133.0, 130.1, 129.9, 128.six, 128.5, 128.1, 127.9, 127.eight, 68.three, 64.0, 63.two, 60.six, 35.five, 27.0, 19.two, 14.9. IR (CH2Cl2) n (cm-1) 3356, 3032, 2959, 1724, 1470, 1408, 1261, 1223, 1111, 1053. HRMS (ESI, TOF): mz = 641.3063 calcd For C37H45N2O6Si [MH] 641.3047. The diastereoselectivity was 62:1.0, determined by Chiral HPLC (Chiralcel OD, HexiPrOH 93:7, 1 mLmin, 25 ), tr ten.two min (minor diastereomer), tr 14.3 min (big diastereomer).NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTypical Process for the Hydrogenolysis and Benzylation with the AlcoholTo Raney ickel ( 0.three g, prewashed with.
