[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1)(=[NH:4])=[O:3].[OH-].[Na+].C(OCC)(=O)C>C1COCC1.Cl>[NH2:11][C:7]1[CH:6]=[C:5]([S:2]([CH3:1])(=[NH:4])=[O:3])[CH:10]=[CH:9][CH:8]=1A solution of 200 mg (1.00 mmol) of (RS)-S-methyl-S-(3-nitrophenyl)sulfoximide in 20 ml of THF is mixed at room temperature with 8 ml of an approximately 10% solution of Ti(III)Cl in 20-30% hydrochloric acid. After 3 hours, another 2 ml of the approximately 10% solution of Ti(III)Cl in 20-30% hydrochloric acid is added and stirred overnight at room temperature. The batch is made basic with 1N NaOH solution and mixed with ethyl acetate. It is filtered, and the filter cakes are washed with ethyl acetate/MeoH (3:2). The organic solvent is drawn off in a rotary evaporator, and the residue is extracted from ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The residue that is obtained is purified by chromatography (DCM/EtOH 95:5). 0.82 mg (0.48 mmol, corresponding to 48% of theory) of the product is obtained.
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