Sulfuric Acid → tert-butyl (6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 258002Notes

Reaction equation

OS(O)(=O)=O.[CH3:6][C:7]([O:9][CH2:10][C:11]1[CH2:20][S:19][C@@H:14]2[C@H:15]([NH2:18])[C:16](=[O:17])[N:13]2[C:12]=1[C:21]([OH:23])=[O:22])=[O:8].[CH3:24][C:25](=[CH2:27])[CH3:26]>O1CCOCC1>[NH2:18][C@@H:15]1[C:16](=[O:17])[N:13]2[C:12]([C:21]([O:23][C:25]([CH3:27])([CH3:26])[CH3:24])=[O:22])=[C:11]([CH2:10][O:9][C:7](=[O:8])[CH3:6])[CH2:20][S:19][C@H:14]12

Participants

Conditions

Temperature: 30 °C

Procedure

Dry dioxane was freed from peroxide by passage through a column of neutral activated alumina. To 100 ml of this solvent was added, in turn, with ice-cooling 10 ml of concentrated H2SO4, 10.9 g of 7-ACA and 50 ml of liquid isobutylene. The mixture was sealed in a pressure bottle, stirred at 30° C. for 2 hours, poured into excess of ice-cold aqueous sodium bicarbonate solution. The solution was extracted with ethyl acetate. The combined ethyl acetate extract was washed with brine and dried over sodium sulfate. Evaporation of the filtrate under reduced pressure gave a light brown foam, 8.3 g (63%) of t-butyl 7β-amino-3-acetoxymethyl-3-cephem-4-carboxylate.

Workup

customThe mixture was sealed in a pressure bottle
additionpoured into excess of ice-cold aqueous sodium bicarbonate solution
extractionThe solution was extracted with ethyl acetate
extractionThe combined ethyl acetate extract
washwas washed with brine
dry with materialdried over sodium sulfate
customEvaporation of the filtrate under reduced pressure

Sources & evidence

ORD record: ord-167742f50ea04818900266b5617c93cf
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05264429

Reaction notes

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