反应详情

To a mixture of (1R,3S,5R)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester (750 mg, 3.30 mmol), (2S)-2-amino-2-(3-chloro-2-fluorophenyl)ethan-1-ol (746 mg, 3.30 mmol) and HBTU (1.75 g, 4.62 mmol) in CH2Cl2 (30 mL) was added under nitrogen DIPEA (2.31 mL, 13.20 mmol). The reaction mixture was stirred at RT overnight. CH2Cl2 and water were added, the layers were separated and the aqueous one back-extracted with CH2Cl2 (×3). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:1 to EtOAc) to give the desired compound as a colorless oil. MS (UPLC/MS): 399.3/401.3 [M+H]+, 443.4/445.3 [M+HCOO]−; tR (HPLC conditions a): 3.28 min.

1. additionwas added under nitrogen DIPEA (2.31 mL, 13.20 mmol)
2. customthe layers were separated
3. extractionthe aqueous one back-extracted with CH2Cl2 (×3)
4. dry with materialThe combined organic extracts were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:1 to EtOAc)