Ethyl Acetate → HCID 131714456, compound

HRID 638084Notes

Reaction equation

HRID 638084 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:25][OH:26])[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O-:22])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:28]([O:31][CH2:32][CH3:33])(=[O:30])C.CN(C)[C:36](=[O:38])[CH3:37]>>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:25][OH:26])[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O:22][CH:36]([O:38][C:28]([O:31][CH2:32][CH3:33])=[O:30])[CH3:37])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 31374DimethylacetamideHCID 131714457HCID 131714457, compound

Product 1

HCID 131714456HCID 131714456, compound

Conditions

Temperature
5 °C

Procedure

1-DL-Iodoethyl ethyl carbonate (22 g) was added dropwise to a solution of sodium 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (15 g) in N,N-dimethylacetamide (120 ml) at 5°-7° C., and the mixture was stirred at 5° C. for 30 minutes. To the reaction mixture was added ethyl acetate (200 ml), followed by filtration. The filtrate was washed with water and an aqueous sodium chloride, and then dried over magnesium sulfate. After removal of the solvent, the residue was washed with ethyl acetate and dried in vacuo to give DL-1-ethoxycarbonyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (7.4 g), mp 126°-130° C.

Workup

  1. filtrationfollowed by filtration
  2. washThe filtrate was washed with water
  3. dry with materialan aqueous sodium chloride, and then dried over magnesium sulfate
  4. customAfter removal of the solvent
  5. washthe residue was washed with ethyl acetate
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f79339f87d3f4f0b9c88c7b08443f809
Source dataset
uspto-grants-1985_12
Patent number
US04559334

Reaction notes

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