摘要 |
<p>1382756 Reacting 3-methyl-3-hydroxycepham compounds ELI LILLY & CO 18 June 1973 [30 June 1972] 28799/73 Heading C2C A process for treating a cepham compound comprises reacting a 3-methyl-3-hydroxy cepham compound of formula with a halogen reagent which is PX 5 or SOX 2 (X = Cl or Br) in the presence of at least one mole of an alkaline agent which is a tertiary amine or an inorganic alkaline salt per mole of the cepham compound and at 60-150‹ C., to form a mixture comprising a compound of formula a compound of formula and a compound of formula wherein R is the residue of an imide derived from a dicarboxylic acid, and R 1 is a carboxy protecting group. The halogen reagent is preferably present in an amount from 1À1 to 2À0 moles per mole of cepham compound and the tertiary amine is preferably present in an amount from 1À0 to 2-0 moles per mole of cepham compound. The tertiary amine is preferably triethyl amine. The following reactions are exemplified (i) the conversion of methyl 7-phthalimido-3α- methyl - 3# - hydroxycepham - 4 - carboxylate to a mixture of methyl 7-phthalimido-3α-methyl - 3# - chlorocepham - 4 - carboxylate, methyl 7 - phthalimido - 3α- methyl - 3 - cepham - 4- carboxylate and methyl 6 - phthalimido - 2α- chloromethylpenam - 2# - methyl - 3 - carboxylate, (ii) the conversion of p-nitrobenzyl 7- phthalimido - 3α- methyl - 3# - hydroxycepham- 4-carboxylate to compounds analogous to those obtained in (i), and (iii) the conversion of pmethoxybenzyl 7 - phthalimido - 3α- methyl- 3# - hydroxycepham - 4 -carboxylate to compounds analogous to those obtained in (i).</p> |