Potassium Carbonate → 2,2-dimethylpropanoyloxymethyl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 247751Notes

Reaction equation

HRID 247751 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:41][CH2:42]I)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N: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][CH2:42][O:41][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[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 104401Iodomethyl pivalateHCID 172973533HCID 172973533, compound

Product 1

HCID 886702192,2-dimethylpropanoyloxymethyl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 75.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1-propenyl)-3-cephem-4-carboxylic acid (Ia, R2 =CH3, R3 =H) (E/Z=1/17, 90 mg, 0.21 mmole) and potassium carbonate (44 mg, 0.32 mmole) in DMF (3 ml) was added at 0° C. pivaloyloxymethyl iodide (77 mg, 0.32 mmole). The mixture was stirred at 0° C. for 40 minutes, diluted with ethyl acetate (20 ml), washed with water, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was dissolved in CHCl3 and chromatographed on a silica gel column (silica gel: 3 g) by eluting with 1% methanol in CHCl3 to yield 85 mg (75%) of the title compound. Mp. 100°-104° C. Estimated purity 90% (by HPLC).

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in CHCl3
  5. customchromatographed on a silica gel column (silica gel: 3 g)
  6. washby eluting with 1% methanol in CHCl3

Sources & evidence

ORD record
ord-0fcc8d974a5e491fb94ce198b732276d
Source dataset
uspto-grants-1987_11
Patent number
US04708955

Reaction notes

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