Dry MeOH) in MeOH (1 mL), was added AcOH (0.three mL) as well as a
Dry MeOH) in MeOH (1 mL), was added AcOH (0.three mL) in addition to a resolution of 9 (64.0 mg, 0.1 mmol) in MeOH (1 mL). The remedy was degassed and stirred beneath a slightly positive pressure of hydrogen (balloon) at 23 for 16 h. The reaction was then filtered by means of a quick pad of Celite, and washed with CH2Cl2. The mixture was concentrated in vacuo and the residue was redissolved in CH2Cl2 and was neutralized by anhydrous Na2CO3. The solvent was removed by vacuum along with the crude product was subjected to benzyl protection with no further purification. Below Ar atmosphere, to a option in the hydrogenated crude solution (0.15 mmol) in anhydrous THF was added NaH (four.eight mg, 0.four mmol). 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 solution was extracted with EtOAc (3 times). The combined organic layers had been dried with MgSO4, and concentrated in vacuo. Purification with the residue by flash CDKN1B Protein web chromatography on silica gel, eluting with 1.0 two.five MeOHCH2Cl2 gave the desired item as a white foamy strong.(2S,3S)-1-(Benzyloxy)-4-((tert-butyldiphenylsilyl)oxy)-3-methylbutan-2-amine (syn-13) The compound was prepared according to the standard hydrogenolysis and benzylation process. Purification by flash chromatography afforded syn-13 as a white foamy solid (22.2 mg, 50 yield in two steps). 1H NMR (400 MHz, CDCl3) 7.71 7.65 (m, 4H), 7.48 7.28 (m, 11H), four.55 (d, J = four.eight Hz, 2H), three.77 three.60 (m, 3H), 3.47 (dd, J = 9.three, 7.six Hz, 1H), 3.18 (td, J = 7.two, three.four Hz, 1H), two.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.six, 133.4, 133.three, 129.7, 128.4, 127.8, 127.7, 73.three, 72.eight, 66.eight, 53.9, 38.1, 27.0, 19.two, 13.9.J Org Chem. Author manuscript; offered 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 ready according to the standard hydrogenolysis and benzylation process. Purification by flash chromatography afforded anti-13 as a white foamy strong (22.three mg, 50 yield in two steps). 1H NMR (400 MHz, CDCl3) 7.70 7.67 (m, 4H), 7.49 7.28 (m, 11H), 4.54 (s, 2H), 3.68 three.58 (m, 2H), 3.56 three.49 (m, 1H), 3.38 (dd, J = ten.2, six.five Hz, 1H), three.26 (br, 1H), 1.83 (br, 1H), 1.51 (br, 2H), 1.08 (s, 9H), 0.92 (d, J = six.9 Hz, 3H); 13C NMR (one hundred MHz, CDCl3) 138.5, 135.6, 133.8, 133.7, 129.6, 128.4, 127.7, 127.6, 74.three, 73.two, 66.8, 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. Hence, the relative stereochemistry assignment was confirmed.CDCP1 Protein supplier Common Procedure for the Preparation of -Amino AcidTo Raney ickel ( 1.5 g, prewashed with dry MeOH) in MeOH (10 mL), was added AcOH (3 mL) plus a resolution of 9 (1.44 g, 2.25 mmol) in MeOH (10 mL). The solution was degassed and stirred under a slightly constructive pressure of hydrogen (balloon) at 23 for 16 h. The reaction was then filtered by way of a brief 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 also the crude solution was subjected to Fmoc-protection with no additional purification. To a solution of the above crude produc.