Ammonium Chloride → HCID 12822421, compound

Participants

Reaction Steps

To a solution of trans 3-azidomethyl-4-tritylthio-2-azetidinone (10.0 g, 47.5 mmol) in dry methanol (500 ml) was added ammonium chloride (19.0 g) and zinc powder (1.0 g) and the suspension was stirred at room temperature for 5 h. The reaction mixture was filtered and evaporated. The residue was partitioned between 1N hydrochloric acid and benzene. The aqueous layer was basified with 1M sodium bicarbonate and extracted with methylene chloride. The extracts were washed with brine, dried (MgSO4) and evaporated in vacuo. The crude amine crystallized from ether, 14.05 g (79%); mp 139°-139.5° C.; Anal. calcd for C23H22N2OCl.1/4 CH2Cl2 : C 70.56, H 5.73, N 7.08; Found: C 70.68, H 5.94, N 7.27; ir (CHCl3) νmax : 3400 and 1760 cm-1 ; 1Hmr (CDCl3) δ: 7.35 (15H, m), 5.15 (1H, m), 4.3 (1H, bs), 2.7-3.5 (3H, m) and 1.3 ppm (2H, m).

Provenance & Evidence