Methane → Cefdinir monohydrate

HRID 969252

Reaction equation

HRID 969252 reaction equation
[CH2:1]=[CH:2][C:3]1[CH2:23][S:22][C@@H:6]2[C@H:7]([NH:10][C:11](/[C:13](/[C:16]3[N:20]=[C:19]([NH2:21])[S:18][CH:17]=3)=[N:14]\[OH:15])=[O:12])[C:8](=[O:9])[N:5]2[C:4]=1[C:24]([OH:26])=[O:25].C(=O)(O)[O-:28].[Na+].C>O>[CH2:1]=[CH:2][C:3]1[CH2:23][S:22][C@@H:6]2[C@H:7]([NH:10][C:11](/[C:13](/[C:16]3[N:20]=[C:19]([NH2:21])[S:18][CH:17]=3)=[N:14]\[OH:15])=[O:12])[C:8](=[O:9])[N:5]2[C:4]=1[C:24]([OH:26])=[O:25].[OH2:28]

Participants

5

Reactant 3

HCID 297MethaneHCID 516892Sodium BicarbonateHCID 6915944Cefdinir

Product 1

HCID 11993766Cefdinir monohydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

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.

Workup

  1. washeluted with 20% aqueous acetone
  2. concentrationconcentrated to 200 ml
  3. customwas adjusted to pH 2.2 at 15° C. with 10% hydrochloric acid
  4. filtrationThe resultant crystals were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ad9dcb1ebd824545b2dd18942824fe49
Source dataset
uspto-grants-2007_12
Patent number
US07307072B2

Linked notes

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