Hydrochloric Acid → (3-oxo-1H-2-benzofuran-1-yl) (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 247033Notes

Reaction equation

HRID 247033 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+].Br[CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:34](=[O:35])[O:33]1.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:32]3[C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:34](=[O:35])[O:33]3)=[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 962181(3H)-Isobenzofuranone, 3-bromo-HCID 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 88638143(3-oxo-1H-2-benzofuran-1-yl) (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 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)-acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylate (100 mg) was dissolved in dimethylformamide (1 ml). 3-Bromophthalide (69 mg) was added to the solution. After stirring for one hour 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) and saturated aqueous NaCl (10 ml×2), 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 well filtered, and dried under reduced pressure to give the title compound (45 mg).

Workup

  1. customThe resulting ethyl acetate layer was separated
  2. washwashed successively with dil. HCl (10 ml) and saturated aqueous NaCl (10 ml×2)
  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. filtrationwell filtered
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-f9ae1b6ea7944dfd8a91f95ff8e86117
Source dataset
uspto-grants-1987_11
Patent number
US04705784

Reaction notes

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