[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](O)=[O:15])[CH:5]=[CH:4][C:3]1=2.CN(C=O)C.[NH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1.O>O=S(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([NH:23][C:24]3[CH:25]=[CH:26][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:32][CH:33]=3)=[O:15])[CH:5]=[CH:4][C:3]1=25,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid 2 (0.20 g, 0.86 mmol) was dissolved in SOCl2 (4.3 mL) at 0° C. A drop of DMF was added and the mixture was stirred for 0.5 h. The SOCl2 was removed under vacuum and the crude acid chloride was dissolved in pyridine (10 mL). Methyl 4-aminobenzoate (0.143 g, 0.947 mmol) and DMAP (0.010 mg, 0.086 mmol) were added and the mixture was heated at 60° C. for 2 h with stirring. The mixture was poured into H2O and the product was extracted with EtOAc; The organic layer was washed successively with HCl (2M), saturated NaHCO3, saturated NaCl, dried over MgSO4, filtrated to give after evaporation methyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoate 3 (0.23 g, 73% yield) as a white solid.
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