Dry MeOH) in MeOH (1 mL), was added AcOH (0.3 mL) and also a
Dry MeOH) in MeOH (1 mL), was added AcOH (0.three mL) in addition to a answer of 9 (64.0 mg, 0.1 mmol) in MeOH (1 mL). The answer was degassed and stirred below a slightly positive stress of hydrogen (balloon) at 23 for 16 h. The reaction was then filtered by way of a quick pad of Celite, and washed with CH2Cl2. The mixture was concentrated in vacuo as well as the residue was redissolved in CH2Cl2 and was neutralized by anhydrous Na2CO3. The solvent was removed by vacuum and the crude product was subjected to benzyl protection with no further purification. Under Ar atmosphere, to a remedy in the hydrogenated crude product (0.15 mmol) in anhydrous THF was added NaH (4.eight mg, 0.four mmol). Right after stirring for five min, BnBr (19 mL, 0.15 mmol) and nBu4NI (11.1 mg, 0.03 mmol) was added plus the mixture was stirred at 23 for 16 h. The reaction was quenched by 1M KHSO4. The aqueous answer was extracted with EtOAc (3 times). The combined organic layers have been dried with MgSO4, and concentrated in vacuo. Purification of the residue by flash c-Raf manufacturer chromatography on silica gel, eluting with 1.0 two.5 MeOHCH2Cl2 gave the desired product as a white foamy strong.(2S,3S)-1-(Benzyloxy)-4-((tert-butyldiphenylsilyl)oxy)-3-methylbutan-2-amine (syn-13) The Kinesin-14 custom synthesis compound was prepared in line with the common hydrogenolysis and benzylation process. Purification by flash chromatography afforded syn-13 as a white foamy strong (22.two mg, 50 yield in two methods). 1H NMR (400 MHz, CDCl3) 7.71 7.65 (m, 4H), 7.48 7.28 (m, 11H), 4.55 (d, J = 4.eight Hz, 2H), three.77 three.60 (m, 3H), 3.47 (dd, J = 9.3, 7.six Hz, 1H), three.18 (td, J = 7.2, three.four Hz, 1H), 2.80 (br, 2H), 1.90 1.79 (m, 1H), 1.08 (s, 9H), 0.94 (d, J = 7.0 Hz, 3H); 13C NMR (one hundred MHz, CDCl3) 138.1, 135.6, 133.4, 133.3, 129.7, 128.4, 127.8, 127.7, 73.3, 72.8, 66.8, 53.9, 38.1, 27.0, 19.two, 13.9.J Org Chem. Author manuscript; accessible in PMC 2014 December 06.Khumsubdee et al.PageNIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscript(2R,3S)-1-(Benzyloxy)-4-((tert-butyldiphenylsilyl)oxy)-3-methylbutan-2-amine (anti-13) The compound was prepared in accordance with the common hydrogenolysis and benzylation procedure. Purification by flash chromatography afforded anti-13 as a white foamy solid (22.three mg, 50 yield in two actions). 1H NMR (400 MHz, CDCl3) 7.70 7.67 (m, 4H), 7.49 7.28 (m, 11H), four.54 (s, 2H), three.68 3.58 (m, 2H), 3.56 three.49 (m, 1H), 3.38 (dd, J = 10.two, six.5 Hz, 1H), 3.26 (br, 1H), 1.83 (br, 1H), 1.51 (br, 2H), 1.08 (s, 9H), 0.92 (d, J = 6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3) 138.five, 135.six, 133.8, 133.7, 129.six, 128.4, 127.7, 127.six, 74.3, 73.2, 66.eight, 29.7, 26.9, 19.3, 11.7. Relative stereochemistry determination of 9: the 13C NMR data of syn-13 matched with reported data39 and differ from that of anti-13. Consequently, the relative stereochemistry assignment was confirmed.Common Process for the Preparation of -Amino AcidTo Raney ickel ( 1.5 g, prewashed with dry MeOH) in MeOH (ten mL), was added AcOH (three mL) and a option of 9 (1.44 g, 2.25 mmol) in MeOH (ten mL). The remedy was degassed and stirred beneath a slightly constructive pressure of hydrogen (balloon) at 23 for 16 h. The reaction was then filtered by means of a short pad of Celite, and washed with CH2Cl2. The mixture was concentrated in vacuo plus the residue was redissolved in CH2Cl2 and was neutralized by anhydrous Na2CO3. The solvent was removed by vacuum and the crude solution was subjected to Fmoc-protection without the need of further purification. To a answer from the above crude produc.
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