反应详情

To a stirred solution of (2S)-2-[(1R,2S)-2-carboxy-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.70 g, 5.6 mmol) in CH2Cl2 (20 mL) were added N-methyl-3-hydroxyphenethylamine hydrobromide (2.44 g, 11.2 mmol), BOP (3.72 g, 8.4 mmol), HOBT (1.29 g, 8.4 mmol), and diisopropylethylamine (4.88 mL, 28.0 mmol) at room temperature. After being stirred at room temperature for 2 hr, the mixture was quenched with 1N HCl (80 mL×3), extracted with AcOEt, dried (MgSO4) and concentrated in vacuo to give a crude oil (3.83 g), which was then purified by flash column chromatography (hexane:AcOEt=1:1) to give (2S)-2-((1R,2S)-2-{[2-(3-hydroxy-phenyl)-ethyl]-methyl-carbamoyl}-1-methylsulfanyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a gum (1.38 g, 56%).

1. customthe mixture was quenched with 1N HCl (80 mL×3)
2. extractionextracted with AcOEt
3. dry with materialdried (MgSO4)
4. concentrationconcentrated in vacuo
5. customto give a crude oil (3.83 g), which
6. customwas then purified by flash column chromatography (hexane:AcOEt=1:1)