Sodium Bicarbonate → Cefazolin deacylated

HRID 2285641

Reaction equation

HRID 2285641 reaction equation
[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9]OC(=O)CC(=O)C)[CH2:7][S:8][C@H:3]12.C(=O)([O-])O.[Na+].[SH:27][C:28]1[S:29][C:30]([CH3:33])=[N:31][N:32]=1>O>[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:27][C:28]3[S:29][C:30]([CH3:33])=[N:31][N:32]=3)[CH2:7][S:8][C@H:3]12

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 117819897beta-Amino-3(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acidHCID 178434161HCID 178434161, compound

Product 1

HCID 6350581Cefazolin deacylatedYield 84.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In water (30 ml) was dissolved 7β-amino-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid (3.14 g) together- with sodium hydrogen carbonate (1.84 g) and 2-mercapto-5-methyl-1,3,4-thiadiazole (1.6 g) and the resultant solution was adjusted its pH to 6.4, followed by stirring for one hour at 60° C. After cooling, the reaction solution was washed with dichloromethane and pH of the aqueous layer was adjusted to 3.5 under ice-cooling, followed by stirring for one hour. The precipitated materials were collected by filtration and washed with water, methanol and acetone in this order, followed by drying to give 7β-amino-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (2.9 g).

Workup

  1. temperatureAfter cooling
  2. washthe reaction solution was washed with dichloromethane and pH of the aqueous layer
  3. temperaturecooling
  4. stirringby stirring for one hour
  5. filtrationThe precipitated materials were collected by filtration
  6. washwashed with water, methanol and acetone in this order
  7. customby drying

Sources & evidence

ORD record
ord-08d6f530993d4d77a871e1ec49768601
Source dataset
uspto-grants-1982_04
Patent number
US04323676

Linked notes

Loading…