Ethyl Acetate → HCID 131713986, compound

HRID 1153785Notes

Reaction equation

HRID 1153785 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:26][O:27][CH2:28][CH3:29])[C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([O-:23])=[O:22])=[C:15]([CH2:18][O:19][CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:31]([O:34][CH2:35][CH3:36])(=[O:33])C.CN(C)[C:39](=[O:41])[CH3:40]>>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:26][O:27][CH2:28][CH3:29])[C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([O:23][CH:39]([O:41][C:31]([O:34][CH2:35][CH3:36])=[O:33])[CH3:40])=[O:22])=[C:15]([CH2:18][O:19][CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 31374DimethylacetamideHCID 131713984HCID 131713984, compound

Product 1

HCID 131713986HCID 131713986, compound

Procedure

To a solution of 500 mg of sodium 7-[2-(2-aminothiazol-4-yl)-2-ethoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylate in 5 ml of N,N-dimethylacetamide were added, with ice-cooling, 395 mg of 1-iodoethyl ethylcarbonate, and then the mixture was stirred at room temperature for 30 minutes. At the end of this time, 50 ml of ethyl acetate were added to the reaction mixture, which was then washed with, in turn, 20 ml of water, 20 ml of a saturated aqueous solution of sodium bicarbonate and 20 ml of an aqueous solution of sodium chloride. The mixture was then dried over anhydrous magnesium sulphate and the solvent was removed by distillation under reduced pressure, giving a residue, which was chromatographed through 20 g of silica gel eluted with ethyl acetate, to afford 460 mg of the title compound.

Workup

  1. temperaturecooling
  2. washwas then washed with, in turn, 20 ml of water, 20 ml of a saturated aqueous solution of sodium bicarbonate and 20 ml of an aqueous solution of sodium chloride
  3. dry with materialThe mixture was then dried over anhydrous magnesium sulphate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customgiving a residue, which
  6. customwas chromatographed through 20 g of silica gel
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-1305aeb5de854e4782fb2ef41629da25
Source dataset
uspto-grants-1984_12
Patent number
US04486425

Reaction notes

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