p-Toluenesulfonic acid → HCID 57518686, compound

Participants

Reaction Conditions

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) (0.300 g, 1.0 mmoles) in isobutyronitrile (7 mL), ZnCl2 (0.0410 g, 3.0 mmol), PTSA (0.057 g, 3.0 mmol) were added under N2 atmosphere. It was heated to 90-95° C. for six hours. After completion of reaction, isopropyl cyanide was removed under reduced pressure and diluted with water and ethyl acetate. The layers are separated and the organic layer was dried over Na2SO4, and concentrated on a rotavapor. The crude material is purified by column. 0.120 g, Off white sticky mass, 1H NMR (400 MHz, CDCl3) δ ppm: 0.81 (s, 3H), 0.97 (s, 3H), 1.21 (s, 3H), 1.34 (d, 6H), 1.43 (s, 9H), 1.70-1.73 (m, 1H), 1.95-2.00 (m, 2H), 2.22-2.25 (m, 2H), 2.55-2.59 (m, 1H), 2.79-2.83 (m, 1H), 3.17-3.19 (m, 1H), 4.51 (s, 1H). m/z (M−100)+H, 252.2.

Provenance & Evidence