Hydrochloric Acid → Cefuroxime Axetil

HRID 2286692Notes

Reaction equation

HRID 2286692 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:10][CH2:11][C:12]1[CH2:13][S:14][C@@H:15]2[C@H:22]([NH:23][C:24](=[O:34])/[C:25](/[C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)=[N:26]\[O:27][CH3:28])[C:21](=[O:35])[N:16]2[C:17]=1[C:18]([OH:20])=[O:19])(=[O:9])[NH2:8].[C:36]([O:39][CH:40](Br)[CH3:41])(=[O:38])[CH3:37].Cl>CN(C)C=O.C(OCC)(=O)C>[C:7]([O:10][CH2:11][C:12]1[CH2:13][S:14][C@@H:15]2[C@H:22]([NH:23][C:24](=[O:34])/[C:25](/[C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)=[N:26]\[O:27][CH3:28])[C:21](=[O:35])[N:16]2[C:17]=1[C:18]([O:20][CH:40]([O:39][C:36](=[O:38])[CH3:37])[CH3:41])=[O:19])(=[O:9])[NH2:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 5479529CefuroximeHCID 111375051-Bromoethyl acetate

Product 1

HCID 6321416Cefuroxime Axetil

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (760 mg, 5.5 mmole) was added to a solution of (6R,7R)-3-carbamoyloxymethyl-7-[(Z)-2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid (4.57 g, 11 mmole) in N,N-dimethylformamide (25 ml) and the mixture was stirred at ca 20° for 25 minutes. 1-Bromoethyl acetate (1.8 g, 11 mmole) in N,N-dimethylformamide (5 ml) was added to the above solution and the reaction mixture was stirred for 40 minutes at ca 20°. The reaction mixture was worked up by pouring it into excess 2 N hydrochloric acid, followed by extraction with ethyl acetate (3 times). The combined organic extracts were washed with 2 N hydrochloric acid and saturated sodium bicarbonate solution, dried (magnesium sulphate) and evaporated in vacuo to yield a foam which was dissolved in ethyl acetate and precipitated from ether.

Workup

  1. stirringthe reaction mixture was stirred for 40 minutes at ca 20°
  2. extractionfollowed by extraction with ethyl acetate (3 times)
  3. washThe combined organic extracts were washed with 2 N hydrochloric acid and saturated sodium bicarbonate solution
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated in vacuo
  6. customto yield a foam which
  7. customprecipitated from ether

Sources & evidence

ORD record
ord-7dd3cf8bad7c4ff58bd285912f1a9ade
Source dataset
uspto-grants-1981_05
Patent number
US04267320

Reaction notes

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