Dry MeOH) in MeOH (1 mL), was added AcOH (0.3 mL) and also a
Dry MeOH) in MeOH (1 mL), was added AcOH (0.3 mL) and a resolution of 9 (64.0 mg, 0.1 mmol) in MeOH (1 mL). The answer was degassed and stirred below a slightly good CDK5 Storage & Stability 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 along with the residue was redissolved in CH2Cl2 and was neutralized by anhydrous Na2CO3. The solvent was removed by vacuum as well as the crude solution was subjected to benzyl protection devoid of further purification. Beneath Ar atmosphere, to a solution of your hydrogenated crude solution (0.15 mmol) in anhydrous THF was added NaH (4.8 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 and the mixture was stirred at 23 for 16 h. The reaction was quenched by 1M KHSO4. The aqueous remedy was extracted with EtOAc (three times). The combined organic layers were dried with MgSO4, and concentrated in vacuo. Purification with the residue by flash chromatography on silica gel, eluting with 1.0 2.5 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 compound was ready as outlined by the standard hydrogenolysis and FGFR1 Compound benzylation process. Purification by flash chromatography afforded syn-13 as a white foamy solid (22.two mg, 50 yield in two measures). 1H NMR (400 MHz, CDCl3) 7.71 7.65 (m, 4H), 7.48 7.28 (m, 11H), 4.55 (d, J = four.eight Hz, 2H), three.77 three.60 (m, 3H), three.47 (dd, J = 9.three, 7.6 Hz, 1H), three.18 (td, J = 7.2, 3.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 (100 MHz, CDCl3) 138.1, 135.six, 133.four, 133.3, 129.7, 128.4, 127.eight, 127.7, 73.three, 72.8, 66.8, 53.9, 38.1, 27.0, 19.two, 13.9.J Org Chem. Author manuscript; available 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 as outlined by the typical hydrogenolysis and benzylation process. Purification by flash chromatography afforded anti-13 as a white foamy solid (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), four.54 (s, 2H), three.68 three.58 (m, 2H), 3.56 three.49 (m, 1H), 3.38 (dd, J = ten.2, 6.5 Hz, 1H), 3.26 (br, 1H), 1.83 (br, 1H), 1.51 (br, 2H), 1.08 (s, 9H), 0.92 (d, J = six.9 Hz, 3H); 13C NMR (100 MHz, CDCl3) 138.5, 135.6, 133.8, 133.7, 129.six, 128.four, 127.7, 127.6, 74.3, 73.2, 66.8, 29.7, 26.9, 19.three, 11.7. Relative stereochemistry determination of 9: the 13C NMR information of syn-13 matched with reported data39 and differ from that of anti-13. As a result, the relative stereochemistry assignment was confirmed.Typical Process for the Preparation of -Amino AcidTo Raney ickel ( 1.five g, prewashed with dry MeOH) in MeOH (ten mL), was added AcOH (3 mL) and also a option of 9 (1.44 g, 2.25 mmol) in MeOH (10 mL). The option was degassed and stirred beneath a slightly positive stress of hydrogen (balloon) at 23 for 16 h. The reaction was then filtered through a quick pad of Celite, and washed with CH2Cl2. The mixture was concentrated in vacuo and also the residue was redissolved in CH2Cl2 and was neutralized by anhydrous Na2CO3. The solvent was removed by vacuum plus the crude item was subjected to Fmoc-protection without having further purification. To a option from the above crude produc.