Sulfuric Acid → (6R,7R)-7-[2-Amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid--water (1/2)

HRID 732849

Reaction equation

HRID 732849 reaction equation
[CH3:1][C:2]1[CH2:21][S:20][C@@H:5]2[C@H:6]([NH:9][C:10]([C@H:12]([NH2:19])[C:13]3[CH2:18][CH:17]=[CH:16][CH2:15][CH:14]=3)=[O:11])[C:7](=[O:8])[N:4]2[C:3]=1[C:22]([OH:24])=[O:23].S(=O)(=O)(O)[OH:26]>O>[CH3:1][C:2]1[CH2:21][S:20][C@@H:5]2[C@H:6]([NH:9][C:10]([CH:12]([NH2:19])[C:13]3[CH2:18][CH:17]=[CH:16][CH2:15][CH:14]=3)=[O:11])[C:7](=[O:8])[N:4]2[C:3]=1[C:22]([OH:24])=[O:23].[OH2:26].[OH2:8]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 38103Cephradine

Product 1

HCID 169372(6R,7R)-7-[2-Amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid--water (1/2)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
52 °C

Procedure

A crystallisation reactor was charged with 3.0 g cephradine and 50 ml water and heated up to T=52° C. Immediately, the combined filtrates and washings were dosed with constant dosing rate in 60 minutes. The temperature was kept at T=52° C. and the pH at 4.80 by titration with 25% sulfuric acid. Then, the temperature was decreased to 25° C. in 30 minutes. The resulting suspension was filtered through a glass filter. The wetcake was washed with 30 ml water and 2×25 ml 80% acetone (acetone/water=80/20 v/v) and dried. 47.0 g cephradine hydrate, with a water content of 3.4%, was obtained.

Workup

  1. customwas kept at T=52° C.
  2. waitThen, the temperature was decreased to 25° C. in 30 minutes
  3. filtrationThe resulting suspension was filtered through a glass
  4. filtrationfilter
  5. washThe wetcake was washed with 30 ml water and 2×25 ml 80% acetone (acetone/water=80/20 v/v)
  6. customdried

Sources & evidence

ORD record
ord-425bcfc214a741f991ef26d6c6bafda4
Source dataset
uspto-grants-2009_09
Patent number
US07588913B2

Linked notes

Loading…