Isopropanol → 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 1923461Notes

Reaction equation

HRID 1923461 reaction equation
C([OH:4])(C)C.[CH3:5][C:6]1[S:10][C:9]([S:11][CH2:12][C:13]2[CH2:30][S:29][C@@H:16]3[C@H:17]([NH:20][C:21]([CH2:23][N:24]4[N:28]=[N:27][N:26]=[CH:25]4)=[O:22])[C:18](=[O:19])[N:15]3[C:14]=2[C:31]([OH:33])=[O:32])=[N:8][N:7]=1.C(=O)([O-])[O-:35].[Na+:38].[Na+]>O>[CH3:5][C:6]1[S:10][C:9]([S:11][CH2:12][C:13]2[CH2:30][S:29][C@@H:16]3[C@H:17]([NH:20][C:21]([CH2:23][N:24]4[N:28]=[N:27][N:26]=[CH:25]4)=[O:22])[C:18](=[O:19])[N:15]3[C:14]=2[C:31]([O-:33])=[O:32])=[N:8][N:7]=1.[OH2:4].[OH2:35].[OH2:4].[OH2:4].[OH2:4].[Na+:38]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 33255Cefazolin

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

Conditions

Temperature
50 °C

Procedure

To a reactor equipped with a jacket were added 5 ml isopropanol, 5 ml water, 10 g cefazolin acid and 1.2 g sodium carbonate, stirred and heated to 50° C. until the solution was clear, the finishing point pH was adjusted to be 6.5, the mixture was directly filtered into a glass crystallizer, agitated, cooled to about 33° C., added serine, turbidness occurred in the solution, hold for 1.0 hours, added anhydrous ethanol in an amount of 15 times as much as the mixture at 2 MPa, cooled to 5-15° C. and hold at the temperature for 1 hour. The resultant was filtered, the filter cake was washed with ethanol, dried at 5° C. for 8 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
  4. temperaturecooled to about 33° C.
  5. additionadded serine, turbidness
  6. additionadded anhydrous ethanol in an amount of 15 times as much as the mixture at 2 MPa
  7. temperaturecooled to 5-15° C.
  8. waithold at the temperature for 1 hour
  9. filtrationThe resultant was filtered
  10. washthe filter cake was washed with ethanol
  11. customdried at 5° C. for 8 hours

Sources & evidence

ORD record
ord-499a7ed03dae4794aa088476ceaef2ab
Source dataset
uspto-grants-2012_05
Patent number
US08178521B2

Reaction notes

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