Trifluoroacetic acid → HCID 10291197, compound

Participants

Reaction Steps

Following general procedure 9, to a stirred solution of the amine (56) (172 mg, 1 equiv.), N-carbobenzyloxy-L-isoleucine (265 mg, 1 equiv.) and EDCI (192 mg, 1 equiv.) in CH2Cl2 (5 mL) was added DMAP (24 mg, 0.2 equiv.). The resultant mixture was stirred at rt for 16 h. The mixture was then diluted with EtOAc and washed successively with 10% citric acid, H2O and brine. The organic extract was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution: 30% EtOAc in hexane to 50% EtOAc in hexane) to afford the desired coupled product. The N-Boc group of the coupled product was then converted to the cyanamide (N—CN) following general procedure 3 (i.e. successive treatment with TFA and BrCN). The crude material was purified by flash chromatography (gradient elution: 25% EtOAc in hexane to 50% EtOAc in hexane) to afford the desired solid benzyl (1S,2S)-1-{[(1-cyano-3-azetidinyl)amino]carbonyl}-2-methylbutylcarbamate (57).

Provenance & Evidence