Hydrochloric Acid → Cefuroxime

HRID 1978133Notes

Reaction equation

HRID 1978133 reaction equation
CC([O:7][C:8]([C:10]1[N:15]2[C:16]([C@@H:18]([NH:19][C:20](/[C:22](/[C:26]3[O:30][CH:29]=[CH:28][CH:27]=3)=[N:23]\[O:24][CH3:25])=[O:21])[C@H:14]2[S:13][CH2:12][C:11]=1[CH2:31][O:32][C:33]([NH2:35])=[O:34])=[O:17])=[O:9])OC(C)=O.C[O-].[Na+].Cl>O1CCCC1.CO>[CH3:25][O:24]/[N:23]=[C:22](\[C:20]([NH:19][C@@H:18]1[C:16](=[O:17])[N:15]2[C:10]([C:8]([OH:9])=[O:7])=[C:11]([CH2:31][O:32][C:33]([NH2:35])=[O:34])[CH2:12][S:13][C@H:14]12)=[O:21])/[C:26]1[O:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6321416Cefuroxime AxetilHCID 10942334Sodium Methoxide

Product 1

HCID 5479529CefuroximeYield 92.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of cefuroxime axetil (20.4 gm, S-isomer >90%, R-isomer <10%) in a mixture of tetrahydrofuran (204 ml) and methanol (14 ml) maintained at −60° C. was added freshly prepared sodium methoxide (1.89 gm, sodium metal was reacted in 28 ml methanol). The reaction contents were stirred for 1 hour and 15% aqueous hydrochloric acid (17 ml) was added. The solvent was distilled at low temperature under vacuum and water was added to the remaining reaction mass. Ethyl acetate was added and the pH level was adjusted to 6.0 with aqueous potassium bicarbonate. The aqueous layer was separated and acidified to pH 1.0 with aqueous hydrochloric acid. The separated solid was filtered, washed with water and dried to yield cefuroxime (15.66 gm).

Workup

  1. customThe reaction contents
  2. distillationThe solvent was distilled at low temperature under vacuum and water
  3. additionwas added to the remaining reaction mass
  4. additionEthyl acetate was added
  5. customThe aqueous layer was separated
  6. filtrationThe separated solid was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-a92f060a3eb24832aa59c55ddcb5a56c
Source dataset
uspto-grants-2001_05
Patent number
US06235896B1

Reaction notes

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