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
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.
Workup
- customThe mixture was evaporated to dryness
- customthe residue was purified by chromatography on silica
- washeluting with a mixture of DCM:MeOH:AcOH:water (120:15:3:2)
- additionThe volume of the product containing fractions
- additionwas added
- customthe mixture was evaporated to dryness
- customThe solid was triturated with diethyl ether
- customcollected by filteration
- customdried at 60° C. under vacuum
Sources & evidence
- ORD record
- ord-54e1283f04694f9fa623c6ad4d5559cb
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067905B2
Reaction notes
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