Hydrochloric Acid → Cefaclor

HRID 484195Notes

Reaction equation

HRID 484195 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1(C)[S:13][C@@H:12]2[C@H:14]([NH:17][C:18]([C@H:20]([NH2:27])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:19])[C:15](=[O:16])[N:11]2[C@H:10]1[C:28]([OH:30])=[O:29].N([O-])=O.[Na+].[ClH:36]>CC(C)=O.C(OCC)(=O)C.O>[NH2:27][C@H:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:18]([NH:17][C@@H:14]1[C:15](=[O:16])[N:11]2[C@@H:12]1[S:13][CH2:9][C:8]([Cl:36])=[C:10]2[C:28]([OH:30])=[O:29])=[O:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6249AmpicillinHCID 8471TriethylamineHCID 23668193Sodium Nitrite

Product 1

HCID 51039Cefaclor

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.6 ml (18.6 mmol) of triethylamine are added to a suspension of 3.5 g (10 mmol) of ampicillin in 15 ml of acetone and stirring takes place for 20 hours, at room temperature. After evaporating the solvent, 30 ml of water, 0.83 g (12 mmol) of sodium nitrite and 20 ml of ethyl acetate are added. The mixture is cooled in an ice bath and is acidified with hydrochloric acid to a pH of 2. The aqueous phase is decanted and the organic phase is washed successively with water and saturated sodium chloride solution, dried over anhydrous magnesium sulphate and evaporated to dryness. A white solid is obtained which corresponds to the title compound. It crystallizes from methanol/water. M.p. 167°-169° C.

Workup

  1. customfor 20 hours
  2. customat room temperature
  3. additionare added
  4. temperatureThe mixture is cooled in an ice bath
  5. customThe aqueous phase is decanted
  6. washthe organic phase is washed successively with water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-5dfe2fc77d7c48c8bfc8cb68ed332052
Source dataset
uspto-grants-1993_07
Patent number
US05229509

Reaction notes

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