Sodium Chloride → HCID 86756434, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(2-methyl-1-propyl)hexanoic acid (172 mg, 0.546 mmol) in 1 mL DMF is added diethyl cyanophosphonate (98 mg, 0.60 mmol) followed by NMM (61 mg, 0.60 mmol). Stirring is continued for 30 min at 0° C. (2S)-2-Amino-5-(nitroimino-amino)methylaminopentanoic acid 1,3-thiazol-2-ylamide hydrochloride (203 mg, 0.60 mmol) is added followed by additional NMM (122 mg, 1.20 mmol). 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-diethyl 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 (5% methanol-dichloromethane) provides 166 mg of (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(2-methyl-1-propyl)hexanoic Acid [(1S)-4-(nitroimino-amino)methylamino-1-(1,3-thiazol-2-ylcarbamoyl)-1-butyl]amide as a foam.

Provenance & Evidence