Hydrochloric Acid → Cefuroxime

HRID 1978134Notes

Reaction equation

HRID 1978134 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.[O-]CC.[Na+].Cl>O1CCCC1.C(O)C>[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 2723922Sodium ethoxideHCID 6321416Cefuroxime Axetil

Product 1

HCID 5479529Cefuroxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

Cefuroxime axetil (20.4 gm, predominantly S-isomer) was dissolved in a mixture of tetrahydrofuran (204 ml) and ethyl alcohol (58 ml). The solution was cooled to −60° C., sodium ethoxide (6.59 gm) was added in portions and the reaction mixture was stirred for 1 hour. Aqueous hydrochloric acid was added and the procedure described in Example 1 was followed to obtain cefuroxime (15.67 gm).

Sources & evidence

ORD record
ord-adf6e006bffa418ea530d1b6a5532d36
Source dataset
uspto-grants-2001_05
Patent number
US06235896B1

Reaction notes

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