Water → Cefazolin

HRID 1470209Notes

Reaction equation

HRID 1470209 reaction equation
OC1C=CC=CC=1/C=[N:5]\[C@@H:6]1[C:13](=[O:14])[N:12]2[C@@H:7]1[S:8][CH2:9][C:10]([CH2:27][S:28][C:29]1[S:30][C:31]([CH3:34])=[N:32][N:33]=1)=[C:11]2[C:15]([O:17]CC1C=CC(OC)=CC=1)=[O:16].O.CS([O:44][C:45](=O)[CH2:46][N:47]1[CH:51]=[N:50][N:49]=[N:48]1)(=O)=O.ClCCl>C(OC)(C)(C)C>[N:47]1([CH2:46][C:45]([NH:5][C@@H:6]2[C:13](=[O:14])[N:12]3[C@@H:7]2[S:8][CH2:9][C:10]([CH2:27][S:28][C:29]2[S:30][C:31]([CH3:34])=[N:32][N:33]=2)=[C:11]3[C:15]([OH:17])=[O:16])=[O:44])[CH:51]=[N:50][N:49]=[N:48]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 90408311HCID 90408311, compoundHCID 178491528HCID 178491528, compound

Product 1

HCID 33255Cefazolin

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A reactor is charged with (6R,7R)-4-methoxybenzyl 7-((Z)-(2-hydroxybenzylidene)amino)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (1 eq), water (6-9 weight % relative to the Schiff base), 2-(1H-tetrazol-1-yl)acetic methanesulfonic anhydride (2.5 eq) and dichloromethane (1.75 mL per gram of Schiff base). The mixture is stirred for three hours at room temperature, then added to methyl tertiary butyl ether over the course of 2-3 hours, resulting in the formation of a solid. The solid is filtered and the filter cake was washed with additional methyl tertiary butyl ether. The filtered solid is deprotected using conventional methods and dried under vacuum to yield the title compound.

Workup

  1. customresulting in the formation of a solid
  2. filtrationThe solid is filtered
  3. washthe filter cake was washed with additional methyl tertiary butyl ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f45306c19bb2418d8e453ffade77ba35
Source dataset
uspto-grants-2015_04
Patent number
US09006421B2

Reaction notes

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