[C:1]1([C:7](C)(O)[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:14][NH:15][O:16][CH3:17].ON1C2C=CC=CC=2N=N1.CN1CC[O:32][CH2:31]C1.C(N=C=NCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:14][N:15]([O:16][CH3:17])[C:31](=[O:32])[CH:8]([OH:10])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1A solution of 2.0 g (12 mmol) of phenyllactic acid, 1.17 g (12 mmol) of N,O-dimethylhydroxylamine hydrochloride, and 1.78 g (13 mmol) of 1-hydroxybenzotriazole in 20 ml of dimethylformamide was treated sequentially with 2.77 ml (25 mmol) of 4-methylmorpholine and 2.53 g (13 mmol) of N-ethyl-N'-(dimethylaminoethyl)carbodiimide. After being stirred at ambient temperature overnight, the solution was diluted with ethyl acetate; washed sequentially with water, 10% citric acid, aqueous NaHCO3, and saturated brine; dried over MgSO4; and concentrated in vacuo to give 2.5 g (100%) of the crude desired compound. 1H NMR (CDCl3) δ 2.85 (dd, J=14, 7 Hz, 1H), 3.08 (dd, J=14, 4 Hz, 1H), 3.23 (s, 3H), 3.72 (s, 3H), 4.62 (m, 1H), 7.2-7.3 (m, 5H). Mass spectrum (M+H)+ =210.
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