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

HRID 2352091Notes

Reaction equation

HRID 2352091 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:26]/[OH:27])/[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+].C1OCCOCCOCCOCCOCCOC1.[C:52]([O:58][CH:59](I)[CH3:60])(=[O:57])[C:53]([CH3:56])([CH3:55])[CH3:54]>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:26]/[OH:27])/[C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([O:23][CH:59]([O:58][C:52](=[O:57])[C:53]([CH3:56])([CH3:55])[CH3:54])[CH3:60])=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 133930641-Iodoethyl 2,2-dimethylpropanoateHCID 14052497(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 150176881-(2,2-dimethylpropanoyloxy)ethyl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-[(Z)-1-propenyl]-3-cephem-4-carboxylic acid (250 mg, 0.61 mmol), K2CO3 (124 mg, 0.90 mmol) and 18-crown-6 (24 mg) in DMF (2.5 ml) was added 1-pivaloyloxyethyl iodide (461 mg, 1.8 mmol) at 5° C. and the mixture was stirred for 45 min at the same temperature. The mixture was diluted with ethyl acetate, washed with water and evaporated under reduced pressure. The residue was chromatographed on a column of silica gel (10 g) and the column was eluted with chloroform containing 1% methanol. The fractions containing the desired product were combined and evaporated under reduced pressure. The residue was dissolved in a small amount of benzene and freeze-dried to give 72 mg (21%) of the product as an amorphous powder.

Workup

  1. washwashed with water
  2. customevaporated under reduced pressure
  3. customThe residue was chromatographed on a column of silica gel (10 g)
  4. washthe column was eluted with chloroform containing 1% methanol
  5. additionThe fractions containing the desired product
  6. customevaporated under reduced pressure
  7. dissolutionThe residue was dissolved in a small amount of benzene
  8. customfreeze-dried

Sources & evidence

ORD record
ord-00be4f1f73154e18b9b8eb6bc41a8ac0
Source dataset
uspto-grants-1989_10
Patent number
US04874856

Reaction notes

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