Sulfuric Acid → HCID 11771800, compound

HRID 1856487Notes

Reaction equation

HRID 1856487 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:15])[CH:10]2[NH2:14])[C:7]=1[C:16]([OH:18])=[O:17])(=[O:3])[CH3:2].S(=O)(=O)(O)O.[CH3:24][C:25](=[CH2:27])[CH3:26].C(=O)(O)[O-].[Na+]>O1CCOCC1>[C:25]([O:17][C:16]([C:7]1[N:8]2[CH:11]([S:12][CH2:13][C:6]=1[CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH:10]([NH2:14])[C:9]2=[O:15])=[O:18])([CH3:27])([CH3:26])[CH3:24]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 137293-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 11771800HCID 11771800, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (0.04 mole) is added to 100 ml of dioxane, 10 ml of concentrated sulfuric acid and 50 ml of liquid isobutylene in a pressure bottle. The mixture is shaken overnight. The bottle is chilled, opened and the contents poured into an ice cold solution of sodium bicarbonate. Extraction of the aqueous phase with ethyl acetate followed by drying and evaporation of the ethyl acetate phase gives the title compound, M.P. 111°-112° C. See J. Med. Chem., 9, 444 (1966).

Workup

  1. temperatureThe bottle is chilled
  2. extractionExtraction of the aqueous phase with ethyl acetate
  3. customby drying
  4. customevaporation of the ethyl acetate phase

Sources & evidence

ORD record
ord-52a97629435040caaa5d9aa98dcb80a7
Source dataset
uspto-grants-1980_08
Patent number
US04219648

Reaction notes

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