Hydrochloric Acid → HCID 58477049, compound

Participants

Reaction Steps

To a solution of tert-butyl {(1S,3S)-3-[(2Z)-2-amino-2-(hydroxyimino)ethyl]-1,2,2-trimethylcyclopentyl}carbamate (prepared in Step-1 example 56)(0.3 g, 1 mmol) in toluene, pyridine (0.079 g, 1 mmol) and cyclohexanecarbonylchloride was added and stirred for 3 hours. The reaction mixture was refluxed for another 12 h. The reaction mixture diluted with ethyl acetate, washed with 0.1N HCl. Ethyl acetate layer was separated, dried and concentrated, residue purified by silica column chromatography using 20% ethyl acetate in hexane. m/z (M+1)−100: 292.1. The product that obtained was dissolved in ethyl acetate. To this a solution of saturated HCl in ethyl acetate (2 mL) was added and reaction mixture was stirred at room temperature for two hours. The volatiles were removed under reduced pressure and triturated with hexane to afford the desired product. 1H NMR (400 MHz, d6-DMSO) δ ppm: 0.8 (s, 3H), 0.9 (s, 3H), 1.2 (s, 3H), 1.42-1.50 (m, 3H), 1.52-1.72 (m, 2H), 1.89-1.92 (m, 5H), 1.95-1.98 (m, 3H), 2.13-2.15 (m, 1H), 2.51-2.54 (m, 1H), 2.74 (m, 1H), 3.02 (m, 1H), 7.95 (bs, 3H).

Provenance & Evidence