Acetic Acid → HCID 131710691, compound

HRID 597160Notes

Reaction equation

HRID 597160 reaction equation
N.C(O)=O.C(O)(=O)C.[C:9]([O:12][CH2:13][C:14]1[CH2:15][S:16][C@@H:17]2[C@H:24]([NH2:25])[C:23](=[O:26])[N:18]2[C:19]=1[C:20]([OH:22])=[O:21])(=[O:11])[CH3:10]>O.CC(C)=O>[C:9]([O:12][CH2:13][C:14]1[C@H:19]([C:20]([OH:22])=[O:21])[N:18]2[C:23](=[O:26])[C@@H:24]([NH2:25])[C@H:17]2[S:16][CH:15]=1)(=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 284Formic AcidHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 131710691HCID 131710691, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

3-Acetoxymethyl-7β-formamidoceph-2-em-4α-carboxylic acid (1.5 g, 0.5 mmol) was dissolved in dioxan (12 ml) containing 50% conc. hydrochloric acid (1.7 ml.) at room temperature. After 2 hr. the excess solvent was removed by freeze-drying to give solid hydrochloride (1.5 g., 100%). Adjustment of the pH to the isoelectric point with a dilute ammonia solution failed to give a precipitate of the zwitterion. The infrared and n.m.r. results on the freeze-dried solution were consistant with the structure of the compound named in the title. Paper electrophoresis was carried out on Whatman No. 1 paper at pH 1.9 [98% formic acid (16.7 ml), glacial acetic acid (84 ml.), acetone (105 ml) and water (495 ml)] at a potential drop of 125 volts/cm for 20 min. The mobility obtained was 5 cm as compared with 3-acetoxymethyl-7β-aminoceph-3-em-4-carboxylic acid which has a mobility of 3.5 cm.

Workup

  1. customto give a precipitate of the zwitterion
  2. customresults on the freeze-dried solution
  3. customThe mobility obtained

Sources & evidence

ORD record
ord-d79e12ac316141a593f95157eb70564d
Source dataset
uspto-grants-1977_03
Patent number
US04013645

Reaction notes

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