[C:1]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH2:13][O:14][CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:48][O:49][CH:50]([O:53][CH3:54])[CH2:51][NH2:52]>C(Cl)Cl.CCOCC>[C:1]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH2:13][O:14][CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:48][O:49][CH:50]([O:53][CH3:54])[CH2:51][NH2:52]To a solution of N-Cbz-O-methylserine (10.8 g, 41.8 mmol) in 500 mL of CH2Cl2 is added Et3N (12.7 g, 125 mmol). The solution is cooled to 0° C. and TBTU (13.5 g, 42 mmol) and aminoacetaldehyde dimethyl acetal (4.83 g, 46 mmol) are added. The solution is stirred for 16 hours. The solution is diluted with 500 mL of ether. The resulting solution is washed with water, 1N KHSO4, and sat. NaCl. The title compound (13.7 g, 41.8 mmol) is obtained as a white foam. 1H NMR (CDCl3, 300 MHz) δ7.40 (m, 5H), 6.55 (bs, 1H), 5.66 (bs, 1H), 5.32 (m, 1H), 5.13 (s, 2H), 4.32 (m, 2H), 3.79 (dd, 1H), 3.44 (m, 2H), 3.40 (m, 9H).
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