Hydrochloric Acid → 1-acetyloxyethyl (6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 247034Notes

Reaction equation

HRID 247034 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:25]1[N:26]=[CH:27][S:28][CH:29]=1)\[C:5]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([O-:22])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[CH2:13][S:14][C@H:9]12)=[O:6].[Na+].[C:31]([O:34][CH2:35][CH2:36]Br)(=[O:33])[CH3:32].Cl.C(OCC)(=O)C>CN(C)C=O>[CH3:1][O:2]/[N:3]=[C:4](/[C:25]1[N:26]=[CH:27][S:28][CH:29]=1)\[C:5]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([O:22][CH:35]([O:34][C:31](=[O:33])[CH3:32])[CH3:36])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 135641-Acetoxy-2-bromoethaneHCID 88637959sodium (6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 886381041-acetyloxyethyl (6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 43.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylate (100 mg) in dimethylformamide (1 ml) was added 2-bromoethyl acetate (54 mg). After stirring for 2 hours at room temperature, the reaction mixture was added to a mixture of dil. HCl (10 ml) and ethyl acetate (20 ml). The resulting ethyl acetate layer was separated, washed successively with dil. HCl (10 ml), phosphate buffer (pH 7, 10 ml×2), and saturated aqueous NaCl (10 ml), dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was dissolved in ethyl acetate (2 ml), and the solution was added dropwise to a petroleum ether-diethyl ether mixture (100 ml) with stirring. Resulting crystals were filtered, and dried under reduced pressure to give the title compound (50 mg).

Workup

  1. customThe resulting ethyl acetate layer was separated
  2. washwashed successively with dil. HCl (10 ml), phosphate buffer (pH 7, 10 ml×2), and saturated aqueous NaCl (10 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (2 ml)
  6. additionthe solution was added dropwise to a petroleum ether-diethyl ether mixture (100 ml)
  7. stirringwith stirring
  8. customResulting crystals
  9. filtrationwere filtered
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-496b0176483c420bb581f9b85d01fcbd
Source dataset
uspto-grants-1987_11
Patent number
US04705784

Reaction notes

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