Acetic Anhydride → HCID 131710690, compound

HRID 597159Notes

Reaction equation

HRID 597159 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][CH:18]=[O:19])[C:15](=[O:20])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1[C@H:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:20])[C@@H:16]([NH:17][CH:18]=[O:19])[C@H:9]2[S:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12764266HCID 12764266, compound

Product 1

HCID 131710690HCID 131710690, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Acetoxymethyl-7β-formamidoceph-3-em-4-carboxylic acid (3.0 g., 1 mmol.) was suspended in dry pyridine (12 ml) at room temperature. Acetic anhydride (1.2 ml.) was added to the stirred suspension and the reaction allowed to proceed for 1 hr. On cooling with ice, the pyridinium salt crystallised and this was filtered off. Treatment of the solid with dilute hydrochloric acid and extraction with ethyl acetate gave the free acid which was obtained as a gum after washing the organic phase with water, drying, and evaporation. The gum (0.61 g 20.3%) could not be crystallised. The spectroscopic properties of the product are consistent with the structure of the compound named in the title νmax (film) 3300 (NH), 1770 (β-lactam), 1730 (OCOCH3), 1675 cm-1 (HCON--) τ (D2O/NaHCO3) 1.82 (singlet, HCO--), 3.52 (singlet, =CH--S), 4.51 and 4.71 (double doublet, J=4 Hz, 6H and 7H protons), 5.22 (collapsed quartet), 5.82 (singlet, CHCO2H) and 7.89 (singlet, CH3COO--).

Workup

  1. temperatureOn cooling with ice
  2. customthe pyridinium salt crystallised
  3. filtrationthis was filtered off
  4. extractionTreatment of the solid with dilute hydrochloric acid and extraction with ethyl acetate
  5. customgave the free acid which
  6. customwas obtained as a gum
  7. washafter washing the organic phase with water
  8. customdrying
  9. customevaporation
  10. customThe gum (0.61 g 20.3%) could not be crystallised

Sources & evidence

ORD record
ord-4af5fc392f5c4255a2c8a44c545836e0
Source dataset
uspto-grants-1977_03
Patent number
US04013645

Reaction notes

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