Intermediates in the synthesis of cephalosporin compounds
AssigneeMerck Sharp & Dohme Corp.
InventorsKristos Adrian Moshos, Valdas Jurkauskas, Giovanni Fogliato, Manuel Scanu, You Seok Hwang
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Abstract
Described herein are crystalline forms of a compound of formula (IIΓ), including toluene solvates off A TD-CLE, as well as processes for the preparation thereof and use thereof in the preparation of cephalosporin compounds such as ceftolozane. Provided herein is a crystalline form of a compound of formula (IIΓ): wherein X is CI, Br, or I; and R1 and R2 are each independently an oxygen protecting group; processes for making the crystalline form, and use of said form in the synthesis of antibacterial cephalosporins such as ceftolozane.
Claims19
A crystalline form of a compound of formula (III):
- wherein PMB is 4-methoxybenzyl;
- and which is a solvate of an aromatic solvent.
A process of making a crystalline form of a compound of formula (III′):
- wherein
- X is Cl or Br;
- and
- R1 and R2 are each independently tert-butyldimethylsilyl, tert-butyl, 4-methoxybenzyl, 2-methoxybenzyl, or triphenylmethyl,
- comprising the step of admixing a non-crystalline form of a compound of formula (III′) and an aromatic solvent to form an admixture comprising the crystalline form of a compound of formula (III′), and
- further comprising the step of cooling the admixture after the step of forming the admixture comprising the crystalline form.
A process of making a compound of formula (V″):
- comprising admixing a crystalline form of a compound of formula (III′):
- wherein
- X is Cl or Br;
- and
- R1 and R2 are each independently tert-butyldimethylsilyl, tert-butyl, 4-methoxybenzyl, 2-methoxybenzyl, or triphenylmethyl;
- with a compound of formula (IV′):
- wherein
- R1 and R2 are each independently an oxygen protecting group;
- R5 and R6 are each independently a nitrogen protecting group;
- and
- A⊖ is a pharmaceutically acceptable anion.
Dependencies are inferred from the claim text.