2-Aminothiazole → HCID 86756440, compound

Participants

Reaction Conditions

Reaction Steps

(2S,3R)-2-tert-Butoxycarbonylamino-3-methyl-5-(nitroimino-amino)methylaminopentanoic acid (123 mg, 0.396 mmol) is dissolved in 1 mL of DMF and cooled to −23° C. TEA (51 μL, 0.37 mmol) is added followed by isobutyl chloroformate (48 μL, 0.37 mmol). After 40 min, 2-aminothiazole is added and the reaction mixture is allowed to come to 25° C. over 18 h. The reaction mixture is added to half-saturated aqueous sodium chloride and extracted with EtOAc. The combined organic layers are washed with 1N HCl, 5% sodium bicarbonate, saturated aqueous sodium chloride, and dried over magnesium sulfate. Concentration in vacuo and purification by chromatography on silica gel (elution with hexanes-EtOAc 1:5 then EtOAc) provides (2S,3R)-2-tert-butoxycarbonylamino-3-methyl-5-(nitroimino-amino)methylaminopentanoic acid 1,3-thiazol-2-ylamide as a foam (101 mg, 66%).

Provenance & Evidence