Aniline → HCID 57224651, compound

Participants

Reaction Conditions

Reaction Steps

Di-isopropylethylamine (2.0 ml) followed by chlorotrimethylsilane (0.73 ml) was added to a stirred solution of 3-amino-N-phenylsulfonylbenzamide hydrochloride (1.8 g, 5.7 mM) in THF (distilled from CaH2 ; 25 ml) under an argon atmosphere. The solution was allowed to stand for 30 minutes then cooled to -10 C. Meanwhile 4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-carboxypyrrolidine (1.84 g, 5 mM) dissolved in tetrahydrofuran (25 ml) was treated with N-methylmorpholine (1.1 ml, 10 mM). This solution was cooled to -15° C. with stirring under an argon atmosphere, and treated with isobutyl chloroformate (0.66 ml, 5 mM) in one portion. After 20 minutes, this solution was added to the solution of the trimethylsilyl derivative of the aniline (prepared above). When the addition was complete, the mixture was stirred for 15 minutes and the solvent evaporated. The residue was partitioned between ethyl acetate (200 ml) and 1M aqueous hydrochloric acid (100 ml). The ethyl acetate layer was washed with hydrochloric acid, brine and dried giving (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(3-phenylsulfonylcarbamoylphenylcarbamoyl)pyrrolidine as a gum which was crystallised from EtOH (2.3 g).

Provenance & Evidence