Hydrochloric Acid → (6R,7R)-7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1463974Notes

Reaction equation

HRID 1463974 reaction equation
[NH2:1][C@@H:2]1[C:23](=[O:24])[N:4]2[C:5]([C:10]([O:12]CC3C=CC([N+]([O-])=O)=CC=3)=[O:11])=[C:6]([Cl:9])[CH2:7][S:8][C@H:3]12.[I-].[Li+].Cl>O1CCCC1>[NH2:1][C@@H:2]1[C:23](=[O:24])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[C:6]([Cl:9])[CH2:7][S:8][C@H:3]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 6452835(4-Nitrophenyl)methyl (6R,7R)-7-amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 6998927(6R,7R)-7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 25.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 3.7 g (10 mmol) of p-nitrobenzyl 7β-amino-3-chloro-3-cephem-4-carboxylate and 61 ml of tetrahydrofuran, was added 8.03 g (60 mmol) of lithium iodide. The resulting reaction mixture was then heated to reflux and allowed to react for about 21/2 hours. The solution was cooled to complete the precipitation of lithium 7β-amino-3-chloro-3-cephem-4-carboxylate. This precipitate was isolated by filtration, slurried in 25 ml of tetrahydrofuran and then acidified to a pH of 3.7 with 1N hydrochloric acid resulting in the formation of a light solid. This solid was isolated by filtration and washed with a 25:3 tetrahydrofuran/water solution to provide 0.59 g of the desired titled product.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas then heated
  3. temperatureto reflux
  4. customto react for about 21/2 hours
  5. temperatureThe solution was cooled
  6. customthe precipitation of lithium 7β-amino-3-chloro-3-cephem-4-carboxylate
  7. customThis precipitate was isolated by filtration
  8. customThis solid was isolated by filtration
  9. washwashed with a 25:3 tetrahydrofuran/water solution

Sources & evidence

ORD record
ord-3711a10fa4ba4ff2bd34efb99b044943
Source dataset
uspto-grants-1994_04
Patent number
US05302711

Reaction notes

Loading…