[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.O=S(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].Cl.[CH2:28]([NH:31][CH2:32][CH3:33])[CH:29]=[CH2:30]>CN(C=O)C.C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[CH:10]=[C:6]([C:7]([N:31]([CH2:28][CH:29]=[CH2:30])[CH2:32][CH3:33])=[O:9])[CH:5]=1
A solution of 1.0 g (4.45 mmol) 5-ethoxy-isophthalic acid mono methyl ester, 10 ml toluene and 0.5 ml SOCl2 is treated with one drop DMF and heated to 80° C. till the evolution of gas ceases. After cooling down the mixture is evaporated, dissolved in 5 ml DCM and added to an at 0° C. stirred mixture of 10 ml 10% aqueous Na2CO3, 0.81 g (6.7 mmol) allyl ethyl amine hydrochloride (see IVb) and 5 ml DCM. After 1 h the layers are separated and the organic layer is washed with 1N HCl, brine, dried with sodium sulfate and evaporated to yield the N-allyl-5-ethoxy-N-ethyl-isophthalamic acid methyl ester. This ester is dissolved in 20 ml MeOH, treated with 15 ml 1N NaOH and stirred for 18 h. The methanol is evaporated, the residue acidified with 1N HCl and extracted with TBME. The organic layer is dried with sodium sulfate and evaporated to yield the title compound.
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