Methanol → HCID 131710408, compound

Participants

Reaction Steps

A solution of pyridine (2.13 ml) in dry methylene dichloride (10 ml) was added, over 5 minutes, to a stirred suspension of phosphorus pentachloride (5.47g) in methylene dichloride (20ml). After 10 minutes, the suspension was cooled to 0°, and a solution of diphenylmethyl 3-(1-ethyltetrazol-5-yl-thiomethyl)-7β-(2-thienylacetamido)-ceph-3-em-4-carboxylate (8.3g) in methylene dichloride (40 ml) was added, dropwise, over 10 minutes. The resulting solution was stirred for a further 1 hour, during which time the temperature was allowed to rise to ca. 23°, and then added, over 10 minutes, to a stirred and cooled (0°) mixture of methanol (30 ml) and methylene dichloride (60 ml). After 15 minutes, N-hydrochloric acid (50 ml) was added, and stirring continues for a further 10 minutes. The organic phase was separated, stirred for 30 minutes with saturated sodium bicarbonate (200 ml), and washed with saturated sodium bicarbonate and brine and treated with some charcoal. The suspension was filtered through a kieselguhr pad, the filtrate dried and evaporated to an oily solid (7.47 g). This material was triturated with ethyl acetate (15ml) to give the amine as a pale-yellow solid (3.854g, 58%); [α]D23 - 213° (c 1.14, CHCl3); λmax. (CHCl3) 265 nm. (ε 7,900); 268.5 nm. (ε 7,900), and 279.5 nm (ε 7,800); τ (DMSO-d6) values include 4.92 (d, J 5 Hz.) and 5.11 (d, J 5 Hz), (6-H and 7H), and 5.72 (q, J 7 Hz.) and 8.61 (t, J 7 Hz.), (CH3CH2 --).

Provenance & Evidence