Ethanol → 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[2-(1H-tetrazol-1-yl)acetyl]amino]-, sodium salt, hydrate (1:1:5), (6R,7R)-

HRID 1923462Notes

Reaction equation

HRID 1923462 reaction equation
C([OH:3])C.ClCCl.[CH3:7][C:8]1[S:12][C:11]([S:13][CH2:14][C:15]2[CH2:32][S:31][C@@H:18]3[C@H:19]([NH:22][C:23]([CH2:25][N:26]4[N:30]=[N:29][N:28]=[CH:27]4)=[O:24])[C:20](=[O:21])[N:17]3[C:16]=2[C:33]([OH:35])=[O:34])=[N:10][N:9]=1.C([O-])(=[O:38])C.[Na+:40]>O>[CH3:7][C:8]1[S:12][C:11]([S:13][CH2:14][C:15]2[CH2:32][S:31][C@@H:18]3[C@H:19]([NH:22][C:23]([CH2:25][N:26]4[N:30]=[N:29][N:28]=[CH:27]4)=[O:24])[C:20](=[O:21])[N:17]3[C:16]=2[C:33]([O-:35])=[O:34])=[N:10][N:9]=1.[OH2:3].[OH2:38].[OH2:3].[OH2:3].[OH2:3].[Na+:40]

Participants

6

Reactant 4

HCID 702EthanolHCID 6344DichloromethaneHCID 33255CefazolinHCID 517045Sodium Acetate

Product 1

HCID 236785985-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[2-(1H-tetrazol-1-yl)acetyl]amino]-, sodium salt, hydrate (1:1:5), (6R,7R)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a reactor equipped with a jacket were added 10 ml ethanol, 50 ml dichloromethane, 20 ml water, 5 g cefazolin acid and 0.9 g sodium acetate, stirred until the solution was clear, the finishing point pH was adjusted to be 7.4, the mixture was directly filtered into a glass crystallizer, agitated for 60 minutes, added dropwise about 20 ml of isopropanol and methanol mixed liquid (the amount of methanol is 3%) and methionine, turbidness occurred in the solution, hold for 4.0 hours, added isopropanol and methanol in a volume 10 times as much as the mixture at 1.5 MPa. The resultant was filtered, the filter cake was washed with acetic acid, dried at 80° C. for 0.5 hours to give cefazolin sodium pentahydrate.

Workup

  1. customTo a reactor equipped with a jacket
  2. filtrationthe mixture was directly filtered into a glass crystallizer
  3. stirringagitated for 60 minutes
  4. additionadded dropwise about 20 ml of isopropanol and methanol mixed liquid (the amount of methanol
  5. additionadded isopropanol and methanol in a volume 10 times as much as the mixture at 1.5 MPa
  6. filtrationThe resultant was filtered
  7. washthe filter cake was washed with acetic acid
  8. customdried at 80° C. for 0.5 hours

Sources & evidence

ORD record
ord-240e96b15b3f4e65a073bba9dac123d3
Source dataset
uspto-grants-2012_05
Patent number
US08178521B2

Reaction notes

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