Dichloromethane → 2-(2-Aminoethylamino)-6-(benzenesulphonylmethyl)-3-(furan-3-yl)benzoic acid hydrochloride
Reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([NH:20][CH2:21][CH2:22][NH:23]C(OC(C)(C)C)=O)[C:14]([C:31]3[CH:35]=[CH:34][O:33][CH:32]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C(Cl)[Cl:44]>>[ClH:44].[NH2:23][CH2:22][CH2:21][NH:20][C:15]1[C:14]([C:31]2[CH:35]=[CH:34][O:33][CH:32]=2)=[CH:13][CH:12]=[C:11]([CH2:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[C:16]=1[C:17]([OH:19])=[O:18]Participants
4
Procedure
6-(Benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoic acid (Intermediate 121, 0.1 g) was added to a solution of trifluoroacetic acid (3 ml) in DCM (3 ml) and the resultant mixture was stirred for 45 minutes. The mixture was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM:MeOH:AcOH:water (120:15:3:2). The volume of the product containing fractions was reduced to 5 mL, concentrated HCl (1 ml) was added and the mixture was evaporated to dryness. The solid was triturated with diethyl ether, collected by filteration and dried at 60° C. under vacuum to give 2-(2-aminoethylamino)-6-(benzenesulphonylmethyl)-3-(furan-3-yl)benzoic acid hydrochloride (0.056 g), as a white solid.