Diethyl Ether → HCID 88784456, compound

Participants

Reaction Steps

A stirred suspension of diphenylmethyl 3-acetylthiomethyl-7β-formamidoceph-3-em-4-carboxylate (0.505 g) in methanol: ether (1:1, 3 ml) at 0° was treated over 10 min. with phosphorous oxychloride (0.468 g). The ice bath was removed and stirring continued for a further 20 min, when a clear solution resulted. The reaction was cooled to 0°, and a white crystalline precipitate appeared. Ether (15 ml) was added and the precipitate filtered off, washed with ether and dried in vacuo to give diphenylmethyl 3-acetylthiomethyl-7β-aminoceph-3-em-4-carboxylate hydrochloride (0.456 g, 89%) as white microcrystals; m.p. 155 -160° (d) [α]D - 91° (c 0.83 in DMSO), λmax (EtOH) 268 nm (ε 8,700)νmax. (Nujol) 1770 (β-lactam), 1720 (CO2R), 1702 cm.-1 (SCOCH3), τ (DMSO-d6) values include 2.60 (m; Ph), 3.02 (s, CHPh2), 7.66 (s, SCOCH3).

Provenance & Evidence