Potassium Carbonate → HCID 88670079, compound

HRID 247758Notes

Reaction equation

HRID 247758 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:27]/[O:28][CH3:29])/[C:8]([NH:10][CH:11]2[C:25](=[O:26])[N:13]3[C:14]([C:22]([OH:24])=[O:23])=[C:15](/[CH:18]=[CH:19]/[CH2:20][CH3:21])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C([O-])([O-])=O.[K+].[K+].[C:36]([O:39][CH:40](Br)[CH3:41])(=[O:38])[CH3:37]>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:27]/[O:28][CH3:29])/[C:8]([NH:10][CH:11]2[C:25](=[O:26])[N:13]3[C:14]([C:22]([O:24][CH:40]([O:39][C:36](=[O:38])[CH3:37])[CH3:41])=[O:23])=[C:15](/[CH:18]=[CH:19]/[CH2:20][CH3:21])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 111375051-Bromoethyl acetateHCID 88669305HCID 88669305, compound

Product 1

HCID 88670079HCID 88670079, compoundYield 49%

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-[(E)-1-butenyl]-3-cephem-4-carboxylic acid (130 mg, 0.3 mmole) and K2CO3 (55 mg, 0.4 mmole) in DMF (2.5 ml) was added at 5° C. 1-bromoethyl acetate (67 mg, 0.4 mmole). The mixture was stirred at 5° C. for 1 hour, diluted with ethyl acetate (25 ml), washed successively with water and an aqueous NaCl solution, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was dissolved in chloroform and chromatographed on a silica gel column with 1% methanol in CHCl3. The desired fractions were combined and concentrated in vacuo to yield 77 mg (49%) of the title compound. Estimated purity 90% (by HPLC). Mp. 110°-115° C.

Workup

  1. additionwas added at 5° C
  2. washwashed successively with water
  3. dry with materialan aqueous NaCl solution, dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in chloroform
  6. customchromatographed on a silica gel column with 1% methanol in CHCl3
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a03efc60f0e041669f1fa9cb6752e0ca
Source dataset
uspto-grants-1987_11
Patent number
US04708955

Reaction notes

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