[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.ClC(OCC)=O.[CH2:29]([N:31]1[CH2:35][CH2:34][CH2:33][C@H:32]1[CH2:36][NH2:37])[CH3:30]>O1CCCC1.ClCCl>[CH2:29]([N:31]1[CH2:35][CH2:34][CH2:33][C@H:32]1[CH2:36][NH:37][C:4](=[O:6])[C:3]1[C:7]([O:14][CH3:15])=[C:8]([O:12][CH3:13])[CH:9]=[C:10]([Br:11])[C:2]=1[NH2:1])[CH3:30]
To a solution of 2-amino-3-bromo-5,6-dimethoxybenzoic acid (0.96 g, 3 mmol) and triethylamine (0.58 ml, 4.2 mmol) in 15 ml tetrahydrofuran/ /dichloromethane (1:1) was added ethyl chloroformate (0.32 ml, 3.4 mmol) at -20° C. After stirring for 45 min. at -20° C. a solution of (2S)-(-)-1-ethyl-2-aminomethylpyrrolidine in 10 ml dichloromethane was added at -20° C. After stirring for 3 h at room temperature the mixture was washed with water and extracted with 0.5M HCl. The aqueous phase was made alkaline and extracted twice with dichloromethane. Drying (Na2SO4) and evaporation gave 0.45 g crude material which was purified by chromatography on a C18 reversed phase column with H2O/MeOH/NH3 40:60:0.3 as eluent to give 0.25 g (22%) pure product as an oil.
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