* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
S-Ztoophenylalaninol (1 g, 3.98 mmol) was dissolved in DCM. To this solution, triethylamine and />-toluenesulphonyl chloride were added slowly at 0 °C. The reaction was then allowed to stir at room temperature overnight. After reaction completion, DCM was evaporated and the crude reaction mixture was purified using column chromatography. The pure product 13a was obtained as white fluffy solid in 78percent yield (1.26g). The pure product 13b was obtained as white solid in 81percent yield
38%
With triethylamine In dichloromethane at 20℃; for 3 h;
Boc- L-phenylalaninol (1.01 g, 4.0 mmol, 1.0 equiv.) and/7-toluenesulfonyl chloride (0.92 g, 4.8 mmol, 1.2 equiv.) were dissolved in dichloromethane (20 mL) and to the solution was added triethylamine (0.84 mL, 6.0 mmol, 1.5 equiv.) at room temperature. The resulting mixture was stirred for 3h, and then the reaction was quenched with saturated ammonium chloride solution. The phases were separated and the water layer was extracted with ether twice. The combined organic phase was washed once with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (0- 20 percent ethyl acetate in hexane) to afford 231 as a white solid (0.61 g, 38percent). Purity 99 percent (HPLC).
38%
With triethylamine In dichloromethane at 20℃; for 3 h;
Boc- L-phenylalaninol (1.01 g, 4.0 mmol, 1.0 equiv.) and />toluenesulfonyl chloride (0.92 g, 4.8 mmol, 1.2 equiv.) were dissolved in dichloromethane (20 mL) and to the solution was added triethylamine (0.84 mL, 6.0 mmol, 1.5 equiv.) at room temperature. The resulting mixture was stirred for 3h, and then the reaction was quenched with saturated ammonium chloride solution. The phases were separated and the water layer was extracted with ether twice. The combined organic phase was washed once with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (0- 20 percent ethyl acetate in hexane) to afford 231 as a white solid (0.61 g, 38percent). Purity 99 percent (HPLC).
38%
With triethylamine In dichloromethane at 20℃; for 3 h;
10250] Boc-E-phenylalaninol (1.01 g, 4.0 mmol, 1.0 equiv.) and p-toluenesulfonyl chloride (0.92 g, 4.8 mmol, 1.2 equiv.) were dissolved in dichloromethane (20 mE) and to the solution was added triethylamine (0.84 mE, 6.0 mmol, 1.5 equiv.) at room temperature. The resulting mixture was stirred for 3 h, and then the reaction was quenched with saturated ammonium chloride solution. The phases were separated and the water layer was extracted with ether twice. The combined organic phase was washed once with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (0-20percent ethyl acetate in hexane) to afford 231 as a white solid (0.61 g, 38percent). Purity 99percent (HPEC).
Reference：
[1] Tetrahedron Letters, 1995, vol. 36, # 14, p. 2505 - 2508
[2] Tetrahedron, 1997, vol. 53, # 13, p. 4769 - 4778
[3] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 503 - 510
[4] Heterocycles, 2009, vol. 77, # 2, p. 865 - 872
[5] Organic and Biomolecular Chemistry, 2014, vol. 12, # 23, p. 3976 - 3985
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 1645 - 1652
[7] Journal of Medicinal Chemistry, 2016, vol. 59, # 9, p. 4210 - 4220
[8] Patent: WO2017/44742, 2017, A1, . Location in patent: Page/Page column 42; 43
[9] Journal of Organic Chemistry, 2001, vol. 66, # 14, p. 4904 - 4914
[10] European Journal of Medicinal Chemistry, 1993, vol. 28, # 1, p. 47 - 61
[11] Patent: WO2008/22345, 2008, A2, . Location in patent: Page/Page column 47
[12] Patent: WO2009/105782, 2009, A1, . Location in patent: Page/Page column 44
[13] Patent: US2015/284352, 2015, A1, . Location in patent: Paragraph 0249; 0250
[14] Chemistry Letters, 1992, # 12, p. 2409 - 2412
[15] Journal of Medicinal Chemistry, 1992, vol. 35, # 7, p. 1259 - 1266
[16] Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6754 - 6759
[17] Journal of Organic Chemistry, 1998, vol. 63, # 22, p. 7764 - 7769
[18] Angewandte Chemie - International Edition, 2000, vol. 39, # 15, p. 2752 - 2754
[19] Tetrahedron, 2007, vol. 63, # 39, p. 9758 - 9763
[20] Synlett, 2007, # 12, p. 1893 - 1896
[21] Journal of Peptide Science, 2011, vol. 17, # 7, p. 527 - 532
[22] Patent: WO2014/52699, 2014, A1, . Location in patent: Page/Page column 222-223
[23] Tetrahedron Asymmetry, 2015, vol. 26, # 1, p. 67 - 72
[24] Organometallics, 2014, vol. 33, # 22, p. 6452 - 6465
[25] RSC Advances, 2017, vol. 7, # 26, p. 15742 - 15746
2
[ 24424-99-5 ]
[ 141403-49-8 ]
Reference：
[1] Tetrahedron, 2007, vol. 63, # 39, p. 9758 - 9763
[2] Angewandte Chemie - International Edition, 2000, vol. 39, # 15, p. 2752 - 2754
[3] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 503 - 510
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 7, p. 1259 - 1266
3
[ 3182-95-4 ]
[ 141403-49-8 ]
Reference：
[1] Tetrahedron, 2007, vol. 63, # 39, p. 9758 - 9763
[2] Angewandte Chemie - International Edition, 2000, vol. 39, # 15, p. 2752 - 2754
[3] Journal of Medicinal Chemistry, 1992, vol. 35, # 7, p. 1259 - 1266
[4] Organometallics, 2014, vol. 33, # 22, p. 6452 - 6465
4
[ 51987-73-6 ]
[ 141403-49-8 ]
Reference：
[1] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 503 - 510
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 23, p. 3976 - 3985
5
[ 63-91-2 ]
[ 141403-49-8 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 23, p. 3976 - 3985
[2] Organometallics, 2014, vol. 33, # 22, p. 6452 - 6465
6
[ 7524-50-7 ]
[ 141403-49-8 ]
Reference：
[1] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 503 - 510
7
[ 2577-90-4 ]
[ 141403-49-8 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 23, p. 3976 - 3985
With lithium aluminium tetrahydride; In tetrahydrofuran; for 4.0h;Reflux;
General procedure: To a stirred solution of N-Boc protected amino alcohol 9 (0.5mg, 1.98mmol) in CH2Cl2 (5mL) were added dry triethylamine (0.3mL, 2.37mmol) and p-toluenesulfonyl chloride (0.452g, 2.37mmol) in the presence of a catalytic amount of 4-dimethylaminopyridine (0.024g,10mol%) at 0C. The reaction mixture was stirred at 25C for 3h and then quenched by addition of 10% NaHCO3. The aqueous layer was extracted with CH2Cl2 (3×20mL) and the combined organic layers were dried over anhydrous Na2SO4, and concentrated to give the crude tosylate, which was then dissolved in dry THF (5mL), and added dropwise to a suspension of LiAlH4 (0.225g, 3mmol) in dry THF (10mL). The mixture was refluxed for 4h and then cooled to 0C after which the excess LiAlH4 was quenched by the addition of EtOAc. It was then treated with aq. 20% NaOH (0.5mL). The white precipitate which formed was filtered off, and the residue was washed with EtOAc (3×10mL). The combined EtOAc layers were dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography over silica gel using CHCl3 as the eluent to afford the corresponding pure N-methyl amine 11. Yield: 0.192g, 65%; [alpha]D25=-10.8 (c 4.2, EtOH); {lit.20 [alpha]D25=-10.9 (c 4.2, EtOH)}; IR (CHCl3, cm-1) 3274, 2917, 2839, 1614,1438; 1H NMR (200MHz, CDCl3): delta 7.15-7.28 (m, 5H), 2.63-2.82 (m, 3H), 2.4 (s, 3H), 1.67 (br s, 1H), 1.08 (d, J=5.9Hz, 3H); 13C NMR (50MHz, CDCl3): delta 139.2, 129.2, 128.4, 126.2, 56.3, 43.3, 33.8, 13.6; Anal. Calcd for C10H15N requires C 80.48; H 10.13; N 9.39%; found C 80.50; H 10.11; N 9.35%.
With sodium azide; In N,N-dimethyl-formamide; at 80℃; for 3.0h;
231 (261 mg, 0.64 mmol, 1.0 equiv.) was dissolved in DMF (1.5 mL), and sodium azide (84 mg, 1.28 mmol, 2.0 equiv.) was added. The reaction mixture was heated to 80 0C and stirred for 3 h. After cooling to room temperature, the solution was partitioned between water (5 mL) and ethyl acetate (10 mL). The organic phase was washed with IN HCl, 5% NaHCO3, and water, dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was chromatographed on silica gel to afford 232 as a white solid (87 mg, 49%). Purity 99% (HPLC). 232 (87 mg, 0.31 mmol) dissolved in ethyl acetate (3 mL) was hydrogenated at atmospheric pressure for 1 h in the presence of 10% Pd/C (20 mg). The catalyst was removed by filtration through Celite, and the filtrate was concentrated in vacuo to give 233, which was used directly in the next step.
49%
With sodium azide; In N,N-dimethyl-formamide; at 80℃; for 3.0h;
231 (261 mg, 0.64 mmol, 1.0 equiv.) was dissolved in DMF (1.5 mL), and sodium azide (84 mg, 1.28 mmol, 2.0 equiv.) was added. The reaction mixture was heated to 80 0C and stirred for 3 h. After cooling to room temperature, the solution was partitioned between water (5 mL) and ethyl acetate (10 mL). The organic phase was washed with IN HCl, 5% NaHCO3, and water, dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was chromatographed on silica gel to afford 232 as a white solid (87 mg, 49%). Purity 99% (HPLC).
49%
With sodium azide; In N,N-dimethyl-formamide; at 80℃; for 3.0h;
10251] 231 (261 mg, 0.64 mmol, 1.0 equiv.) was dissolved in DMF (1.5 mE), and sodium azide (84 mg, 1.28 mmol, 2.0 equiv.) was added. The reaction mixture was heated to 80 C. and stirred for 3 h. Afier cooling to room temperature, the solution was partitioned between water (5 mE) and ethyl acetate (10 mE). The organic phase was washed with iN HC1, 5% NaHCO,, and water, dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was chromatographed on silica gel to afford 232 as a white solid (87 mg, 49%). Purity 99% (HPEC). 232 (87 mg, 0.31 mmol) dissolved in ethyl acetate (3 mE) was hydrogenated at atmospheric pressure for 1 h in the presence of 10% PdC (20 mg). The catalyst was removed by filtration through Celite, and the filtrate was concentrated in vacuo to give 233, which was used directly in the next step.
acetic acid 2-benzenesulfonyl-1-[1-(benzyl-<i>tert</i>-butoxycarbonyl-amino)-2-phenyl-ethyl]-3-<i>tert</i>-butoxycarbonylamino-4-phenyl-butyl ester[ No CAS ]
[3-benzenesulfonyl-4-<i>tert</i>-butoxycarbonylamino-2-hydroxy-1-(4-methoxy-benzyl)-5-phenyl-pentyl]-benzyl-carbamic acid <i>tert</i>-butyl ester[ No CAS ]
acetic acid 2-benzenesulfonyl-1-[1-(benzyl-<i>tert</i>-butoxycarbonyl-amino)-2-(4-methoxy-phenyl)-ethyl]-3-<i>tert</i>-butoxycarbonylamino-4-phenyl-butyl ester[ No CAS ]
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