Sodium Chloride → HCID 86756443, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(2-methyl-1-propyl)butanoic acid (34 mg, 0.12 mmol) in 1 mL anhydrous DMF is added diethyl cyanophosphonate (19 mg, 0.119 mmol) followed by NMM (12 mg). Stirring is continued for 30 min at 0° C. (2S,3R)-2-Amino-3-methyl-5-(nitroimino-amino)methylaminopentanoic acid 1,3-thiazol-2-ylamide hydrochloride (42 mg, 0.119 mmol) is added followed by additional NMM (36 mg). The mixture is heated at 40° C. for 16 h then allowed to cool to 25° C. The reaction mixture is added to half-saturated aqueous sodium chloride and extracted with 1:1 EtOAc-ether. The combined organic layers are washed with pH 4.3 phosphate buffer, 5% aqueous sodium bicarbonate, saturated aqueous sodium chloride, and dried over magnesium sulfate. Concentration and chromatography on silica gel (elution with 5% methanol in dichloromethane) provides 35 mg of (2R,3S)-3-(formyl-tetrahydropyranyloxyamino)-2-(2-methyl-1-propyl)butanoic acid [(1S,2R)-2-methyl-4-(nitroimino-amino)methylamino-1-(1,3-thiazol-2-ylcarbamoyl)-1-butyl]amide as a foam.

Provenance & Evidence