Sodium Iodide → Phthalid-3-yl 7-[2(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate

HRID 1154225Notes

Reaction equation

HRID 1154225 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:25][O:26][CH3:27])[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+].Br[CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:32](=[O:33])[O:31]1.[I-].[Na+].C(OCC)(=O)C>CN(C)C=O.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:25][O:26][CH3:27])[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O:22][CH:30]4[C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[C:32](=[O:33])[O:31]4)=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 131713178Sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate

Product 1

HCID 131713182Phthalid-3-yl 7-[2(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylateYield 51.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium 7-[2-(2-aminothiazol-4yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (2.16 g) in N,N-dimethylformamide (20 ml) were added 3-bromophthalide (1.3 g) and sodium iodide (1.35 g), and the mixture was stirred at ambient temperature for 40 minutes. Thereto was added ethyl acetate (100 ml) and water (50 ml), and the separated ethyl acetate layer was washed with a saturated aqueous solution of sodium bicarbonate and an aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After removal of the solvent, the residue (2.6 g) was chromatographed on silica gel (50 g) using a mixture of benzene and ethyl acetate as an eluent. The fractions containing the desired compound were collected and evaporated to give phthalid-3-yl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (1.4 g).

Workup

  1. washthe separated ethyl acetate layer was washed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialan aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  3. customAfter removal of the solvent
  4. customthe residue (2.6 g) was chromatographed on silica gel (50 g)
  5. additiona mixture of benzene and ethyl acetate as an eluent
  6. additionThe fractions containing the desired compound
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-351ae4830e7847e289b7d71a26f903fd
Source dataset
uspto-grants-1984_12
Patent number
US04487927

Reaction notes

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