Potassium Carbonate → HCID 88669987, compound

HRID 247752Notes

Reaction equation

HRID 247752 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:26]/[O:27][CH3:28])/[C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([OH:23])=[O:22])=[C:15]([CH:18]=[CH:19][CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:35]([O:38][CH:39](Br)[CH3:40])(=[O:37])[CH3:36]>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:26]/[O:27][CH3:28])/[C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([O:23][CH:39]([O:38][C:35](=[O:37])[CH3:36])[CH3:40])=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 111375051-Bromoethyl acetateHCID 172973533HCID 172973533, compound

Product 1

HCID 88669987HCID 88669987, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a mixture of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1-propenyl)-3-cephem-4-carboxylic acid (190 mg, 0.45 mmole) and potassium carbonate (75 mg, 0.54 mmole) in DMF (5 ml) was added at 5° C. 1-bromoethyl acetate** (90 mg, 0.54 mmole). The mixture was stirred at 5° C. for 1.5 hours and diluted with ethyl acetate (20 ml). The dilute was washed successively with water and a saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was dissolved in chloroform and chromatographed on a silica gel column (5 g) with 1% methanol in chloroform. The desired fractions were combined and concentrated. The residue was dissolved in dioxane and lyophilized to yield 103 mg (45%) of the title compound as its dioxane solvate. Mp. 105°-110° C. Estimated purity 85% (by HPLC).

Workup

  1. additionwas added at 5° C
  2. washThe dilute was washed successively with water
  3. dry with materiala saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in chloroform
  6. customchromatographed on a silica gel column (5 g) with 1% methanol in chloroform
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in dioxane

Sources & evidence

ORD record
ord-84ad4a9eb8094858a20f14f24d0e6f2b
Source dataset
uspto-grants-1987_11
Patent number
US04708955

Reaction notes

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