Ethyl Acetate → HCID 70510944, compound

HRID 461947Notes

Reaction equation

HRID 461947 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:32](=[O:33])[N:14]2[CH:15]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[O:21])[C:16](=C)[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=[O:36])C>>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:32](=[O:33])[N:14]2[C:15]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[O:21])=[C:16]([OH:36])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 12877287HCID 12877287, compound

Product 1

HCID 70510944HCID 70510944, compound

Conditions

Temperature
0 °C

Procedure

A solution of 2.5 g. of p-methoxybenzyl 7-phenoxyacetamido-3-methylenecepham-4-carboxylate in 350 ml. of ethyl acetate was cooled in an acetone-dry ice bath. Ozone was bubbled through the cold solution for 8 minutes and then oxygen was passed through the ozonized reaction mixture to expel excess ozone. The intermediate ozonide was decomposed by adding to the reaction mixture 25 g. of sodium bisulfite with stirring at a temperature of about 0° C. The reaction solution was decanted and was washed successively with water, 5% hydrochloric acid and a saturated solution of sodium chloride. The washed mixture was dried and evaporated to yield the reaction product, p-methoxybenzyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate as an amorphous solid.

Workup

  1. customOzone was bubbled through the cold solution for 8 minutes
  2. additionby adding to the reaction mixture 25 g
  3. customThe reaction solution was decanted
  4. washwas washed successively with water, 5% hydrochloric acid
  5. customThe washed mixture was dried
  6. customevaporated

Sources & evidence

ORD record
ord-246a25abeccd4d69bcb28d7a348e7e1d
Source dataset
uspto-grants-1977_12
Patent number
US04064343

Reaction notes

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