Ct. The item can’t be very easily converted to any identified structure.
Ct. The solution cannot be very easily converted to any recognized structure.HSPA5 Storage & Stability NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTypical ALK5 Storage & Stability Process for the -Amination of the AldehydeA modification of reported procedure38 was applied. Dibenzyl azodicarboxylate (90 , 1.29 g, 3.9 mmol) and proline (70 mg, 0.six mmol) in MeCN (10 mL) had been cooled down to -3 . The aldehyde (1.02 g three.0 mmol) was then added plus the mixture was stirred at -3 for two h. The reaction was gradually warmed to 20 within ca. 1 h. The mixture was then cooled to 0 , treated with MeOH (3 mL) and NaBH4 (240 mg, 6.0 mmol) and was stirred for 5 min at 0 . The reaction was quenched by 1M KHSO4. The aqueous option was extracted with EtOAc 3 instances. The combined organic layers had been dried with MgSO4, and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel, eluting with 15 EtOAchexanes gave the preferred alcohol as white foamy solid.J Org Chem. Author manuscript; accessible 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 according to the common -amination procedure catalysed by (R)-Proline. Purification by flash chromatography afforded anti-9 as a white foamy strong (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), 5.37 5.10 (m, 4H), 4.45 4.12 (m, 2H), 3.80 three.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, 157.4, 135.six, 133.three, 133.2, 129.six, 129.eight, 128.7, 128.6, 128.two, 127.9, 127.8, 127.7, 68.62, 65.88, 65.56, 60.37, 35.six, 26.9, 19.three, 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 10.3 min (minor diastereomer), tr 14.4 min (major 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 based on the standard -amidation procedure 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.six Hz, 4H), 7.50 7.24 (m, 16H), 6.96 (s, 1H), 5.30 five.22 (m, 3H), five.13 (dd, J = 12.1, 9.six Hz, 1H), 4.36 4.16 (m, 2H), three.86 three.70 (m, 2H), 3.59 three.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.six, 158.two, 156.8,J Org Chem. Author manuscript; obtainable in PMC 2014 December 06.Khumsubdee et al.Page156.five, 135.9, 135.6, 135.five, 135.4, 133.0, 130.1, 129.9, 128.6, 128.5, 128.1, 127.9, 127.eight, 68.3, 64.0, 63.2, 60.6, 35.5, 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 10.two min (minor diastereomer), tr 14.3 min (major diastereomer).NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTypical Process for the Hydrogenolysis and Benzylation in the AlcoholTo Raney ickel ( 0.3 g, prewashed with.
