Reaction #985265

ord-52f6304a211841e38c522993a859a60c

Reaction equation

C
charcoal
C=CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)/C(=N\O)c3csc(N)n3)[C@H]2SC1
Cefdinir
O=C([O-])O.[Na+]
sodium bicarbonate
→
C=CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)/C(=N\O)c3csc(N)n3)[C@H]2SC1.O
Cefdinir monohydrate

Reactants

—
resultant solution
C
charcoal
C=CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)/C(=N\O)c3csc(N)n3)[C@H]2SC1
Cefdinir
O=C([O-])O.[Na+]
sodium bicarbonate

Reagents

None

Solvents

O
water

Conditions

Temperature
0°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Washeluted with 20% aqueous acetone
  2. 2
    Concentrationconcentrated to 200 ml
  3. 3
    Otherwas adjusted to pH 2.2 at 15° C. with 10% hydrochloric acid
  4. 4
    FiltrationThe resultant crystals were collected by filtration
  5. 5
    Washwashed with water
  6. 6
    Otherdried

Procedure

The monohydrate was prepared as follows: Cefdinir (20.0 g) was added to water (200 ml) and the mixture was adjusted to pH 6.0 with saturated sodium bicarbonate aqueous solution. The resultant solution was subjected to a column chromatography on activated charcoal and eluted with 20% aqueous acetone. Fractions were combined and then concentrated to 200 ml. This solution was adjusted to pH 2.2 at 15° C. with 10% hydrochloric acid and stirred at 0° C. for 30 minutes. The resultant crystals were collected by filtration, washed with water and dried to give crystals of Cefdinir monohydrate. The present inventors investigated physicochemical properties for Cefdinir monohydrate and crystal form A. The results are described below.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07351419B2uspto-grants-2008_04