Diisopropylcarbodiimide → HCID 118204534, compound

Participants

Reaction Steps

(S)-3-(tert-butoxycarbonylamino)-2,2-diethoxyhexanoic acid (8.03 g, 25.1 mmol) was dissolved under nitrogen in 400 mL DMF and HOBt (4.10 g, 30.3 mmol), DIC (7.7 mL, 49.7 mmol) and cyclopropylamine (3.5 mL, 50.0 mmol) were added to the reaction mixture. After stirring for 24 hours at room temperature, the mixture was quenched with 400 mL 5% NaCl and 800 mL EtOAc and the phases were separated. The aqueous phase was extracted with 100 mL EtOAc, the combined organic phases were dried over Na2SO4 and the solvent was removed in vacuo. Purification by column chromatography on silica gel (CHX:EE 10:1→3:1) yielded 3.2 g (S)-tert-butyl 1-(cyclopropylamino)-2,2-diethoxy-1-oxohexan-3-ylcarbamate.

Provenance & Evidence