Ethyl Acetate → HCID 86757661, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of pentafluorophenyl (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(4-phenylcyclohexylmethyl)butanoate (0.25 g, 0.44 mmol), (2S)-2-amino-3,3-dimethylbutanoic acid 1,3-thiazol-2-ylamide (0.10 g, 0.49 mmol), HOBt (6.1 mg, 0.040 mmol) and TEA (0.07 g, 0.67 mmol) in DMF (3 mL) is heated at 41° C. for 18 h. The reaction mixture is poured into a mixture of hexanes (100 mL) and EtOAc (100 mL) and the resulting mixture is washed with water, 1 M aqueous sodium carbonate and water. The organic phase is dried (sodium sulfate) and concentrated in vacuo and the residue is purified by column chromatography on silica gel with EtOAc-hexanes (1:1) as eluent to give 0.12 g (46%) of (2R,3S)-3-(formyltetrahydropyranyloxyamino)-2-(4-phenylcyclohexylmethyl)butanoic acid [(1S)-2,2-dimethyl-1-(1,3-thiazol-2-ylcarbamoyl)-1-propyl]amide as a white solid.

Provenance & Evidence