O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.Cl.[CH2:13]([O:15][C:16](=[O:21])[C@H:17]([CH2:19][SH:20])[NH2:18])[CH3:14].C(N(C(C)C)C(C)C)C.O>C(O)C>[OH:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]2[NH:18][CH:17]([C:16]([O:15][CH2:13][CH3:14])=[O:21])[CH2:19][S:20]2)=[CH:4][C:5]=1[O:6][CH3:7]To a solution of 1.52 g (10 mM) of vanillin (4-hydroxy-3-methoxybenzaldehyde) in 20 mL of absolute ethanol was added a solution of 1.85 g (10 mM) L-cysteine ethyl ester hydrochloride in 15 mL absolute ethanol, containing 1.7 mL (10 mM) of N-ethyldiisopropylamine. The reaction mixture was stirred at room temperature for about six hrs, until no starting material was present when monitored by thin layer chromatography (TLC). After adding 200 mL of water with stirring, the white precipitate was filtered, washed with 2×50 mL water, and vacuum dried. Yield 1.9 g (67%) of 1. 1H NMR (DMSO-d6; ˜1:1 diastereoisomeric mixture at C2)δ (1.22 m, 3H); (3.01 m and 3.15 m, 1H); (3.33 m, 2H); (3.75 s and 3.77 s, 3H); (4.15 m, and 4.38 bs, 2H); (5.40 d and 5.49 d, 1H); 6.79-6.73 m, 2H); 6.83-6.89 m 1H); (7.02 d and 7.12d, 1H); (8.99 s and 9.05 s, 1H). Mass analysis: Calculated for C13H17NO4S:284 [M+H]+. Found: 284.
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