2-Chloro-3-nitropyridine → N-(3-nitro-2-pyridyl)-(-)-S-methyl-L-cysteine methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:9])[C@H:4]([CH2:6][S:7][CH3:8])[NH2:5].Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:9])[C@H:4]([CH2:6][S:7][CH3:8])[NH:5][C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1Participants
4
Procedure
In analogy to Example 2, but using only one mole equivalent of triethylamine, 5 g (27 mmol) of (-)-S-methyl-L-cysteine methyl ester were reacted with 3.51 g (22.5 mmol) of 2-chloro-3-nitropyridine (reaction conditions: 5 hours at 80° C.). Working up was followed by chromatography on silica gel (n-heptane/acetone/methyl t-butyl ether=5:1:1). 3.3 g (45%) of N-(3-nitro-2-pyridyl)-(-)-S-methyl-L-cysteine methyl ester, of melting point 95°-97° C., were obtained.