Ammonia → HCID 70637607, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of 13.1 g. (22 mmoles) of 6-(triphenylmethylamino)-2,2-dimethyl-3-{chloro-[N-(4-methoxybenzyl)imino]methyl}penam in 45 ml. of ethanol-free chloroform, a 1.33 N ammonia solution in chloroform is added all at once. The resulting mixture is stirred 5 minutes at 0° C. and then for 45 minutes at 25° C. The mixture is then filtered, and the filtrate rotoevaporated to an amber oil. Addition of ether (100 ml.) affords a precipitate which is filtered and then taken up in 150 ml. chloroform. The chloroform solution is washed first with 100 ml. 0.5N NaOH; and then with three 150 ml. portions of water. It is then dried over anhydrous sodium sulfate and rotoevaporated to afford the title compound as an orange foam. Rotoevaporation of the filtrate obtained after the ether precipitation procedure affords more of the title compound, as an orange foam. Total yield= 12.05 g. (95%). 1H--NHR (CDCl3 ) ppm (δ) 1.33 (3H, s, 2--CH3); 1.60 (3H, s, 2--CH3); 3.81 (3H, s, --OCH3); 4.17-4.68 (3H, m; 3-, 5- and 6-H); 4.24 (2H, s, --CH2 --), 4H, AB with Ha within 7.2-7.68 multiplet; Hb centered at 6.89, J= 9 HZ. (CH3O--C6H4 --), 7.2-7.68 (15H, m, C6H5). Infrared (CH2Cl2) λmax (μ) 5.62 (s, strong); 5.75-5.83 (broad s, strong); 5.97 (broad s, strong).

Provenance & Evidence