Ammonia → HCID 19810529, compound

Participants

Reaction Steps

The benzyl ester from Example 54 was dissolved in 10 ml of MeOH and hydrogenolyzed (H2 in balloon in the presence of 10% Pd/C, 0.3 g) at room temperature for 3 h. At the end, the catalyst was removed by filtration and the crude product, after removal of MeOH under reduced pressure, was added to a flask containing HOBT (967 mg, 7.16 mmol), Et3N (0.33 ml, 2.4 mmol) in 10 ml of DMF at 0° C. After 5 min, EDAC (458 mg, 2.38 mmol) was added and the reaction was slowly brought to room temperature. At the end of 13 h at room temperature, the contents was poured onto a slurry of aqueous NaHCO3 and AcOEt. The product was extracted and purified by Column chromatography (silica gel, Hexane-AcOEt, 4:1) which gave a mixture of two diastereomers (340 mg, 45%, 1:1 ratio, dl mixture at the benzyl centre): DCI-NH3 -MS, m/z 318 (MH+, 100%).

Provenance & Evidence