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

HRID 2289841Notes

Reaction equation

HRID 2289841 reaction equation
Cl.[NH2:2][CH:3]1[C:15](=[O:16])[N:5]2[C:6]([C:12]([OH:14])=[O:13])=[C:7]([CH:10]=[O:11])[CH2:8][S:9][C@H:4]12.N1C=CC=CC=1>CO>[NH2:2][C@@H:3]1[C:15](=[O:16])[N:5]2[C@@H:4]1[S:9][CH2:8][C:7]([CH:10]=[O:11])=[C:6]2[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 1049PyridineHCID 872037627-Amino-3-formyl-3-cephem-4-carboxylic acid

Product 1

HCID 15385898(6R,7R)-7-amino-3-formyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2.64 g of the hydrochloride of 6-amino-1,4,5a,6-tetrahydro-3-hydroxy-1,7-dioxo-3H,7H-aceto[2,1-b]furo[3,4-d][1,3]thiazine (hydroxylactone of the hydrochloride of 7-amino-3-formyl-3-cephem-4-carboxylic acid) are dissolved in 50 ml of methanol. A solution of 0.78 g of pyridine in 10 ml of methanol is added dropwise to this solution whilst stirring and cooling with ice. The precipitated product is filtered off under nitrogen whilst excluding moisture, washed with a little methanol and dried over a drying agent in vacuo at room temperature. (6R-trans)-7-amino-3-formyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is thus obtained in the form of a light brown powder. IR (KBr): 1799 cm-1 (β-lactam), 1672 cm-1 (CHO), 1606 and 1542 cm-1 (carboxylate) UV spectrum: λmax in H2O=302 nm.

Workup

  1. temperaturecooling with ice
  2. filtrationThe precipitated product is filtered off under nitrogen
  3. washwashed with a little methanol
  4. customdried over a drying agent in vacuo at room temperature

Sources & evidence

ORD record
ord-277a7e3922c944b6911768db7bbbdeaf
Source dataset
uspto-grants-2000_07
Patent number
US06093813

Reaction notes

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