Hydrochloric Acid → HCID 131711399, compound

Participants

Reaction Conditions

Reaction Steps

t-Butyl (6R,7R)-3-formyloxymethyl-7-(2-thienylacetamido)ceph-2-em-4-carboxylate (50 mg.; 0.115 mmole), warm methanol (2 ml) and 2N hydrochloric acid (0.025 ml) were stirred together at 25° C. at an apparent pH of 2. T.l.c. after 2 hours 20 minutes showed a virtually complete reaction. Propylene oxide (0.1 ml) was added and the mixture was stirred at 25° C. for 5 minutes. The mixture was partitioned between ethyl acetate (40 ml) and water (40 ml). The aqueous layer was extracted with ethyl acetate (20 ml) and the combined organic layers were washed with water (2 × 20 ml) and dried over anhydrous sodium sulphate and filtered and evaporated to a gum. This gum was dissolved in ethyl acetate (2 ml) and added dropwise to stirred 40 to 60° petroleum ether (100 ml) to give a pale yellow solid (23mg.; 50%). T.l.c. after work up indicated approximately 20% lactone. τ (d6DMSO) 0.81 (d, J 9Hz; NH), 2.6, 3.0 (mult.; thienyls), 3.5 (broad s; Δ2 2-H), 4.51 (d,d J 9, 5Hz; 7-H), 4.80 (d, J 5Hz; 6-H), 4.92 (broad s; --CH2OH), 5.10 (broad s; 4-H), 5.95 (mult; 3 CH2), 6.20 (s; ##STR5## and 8.55 (s; tBu).

Provenance & Evidence