Diisopropylethylamine → HCID 57070558, compound

Participants

Reaction Steps

A solution of 15(a) (1.53 g. 4.18 mmol) in CH2Cl2 (20 mL) was added to a stirred solution of (2S,4S)-2-aminomethyl-4-BOCsulfanyl-pyrollidine-1-carboxylic acid allyl ester (15(b)) (prepared as described in International Patent Application WO 92/17480. see pages 39-41) (1.32 g. 4.18 mmol) and (iPr)2NEt (1.5 mL. 9.0 mmol) in CH2Cl2 (30 mL) at 0° C. under argon. The resulting solution was allowed to warm to room temperature and stirred for 18 hours. The reaction mixture was then washed with water (100 mL), dried over MgSO4, filtered and concentrated to a viscous white gum. This was then purified by flash chromatography on 9385 SiO2. eluting with a gradient of 35-50% EtOAc/i-Hexane to give (2S,4S)-4-BOCsulfanyl-2-{[3-([1S]-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-benzenesulfonylamino]-methyl }-pyrrolidine-1-carboxylic acid allyl ester (15(c)) as a colourless foam: 2.19 g (81.3%).

Provenance & Evidence