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

HRID 247755Notes

Reaction equation

HRID 247755 reaction equation
[C:1]([O:7][CH2:8]I)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:10][C:11]1[S:12][CH:13]=[C:14](/[C:16](=[N:36]/[O:37][CH3:38])/[C:17]([NH:19][CH:20]2[C:34](=[O:35])[N:22]3[C:23]([C:31]([OH:33])=[O:32])=[C:24](/[CH:27]=[CH:28]\[CH2:29][CH3:30])[CH2:25][S:26][C@H:21]23)=[O:18])[N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[NH2:10][C:11]1[S:12][CH:13]=[C:14](/[C:16](=[N:36]/[O:37][CH3:38])/[C:17]([NH:19][CH:20]2[C:34](=[O:35])[N:22]3[C:23]([C:31]([O:33][CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:32])=[C:24](/[CH:27]=[CH:28]\[CH2:29][CH3:30])[CH2:25][S:26][C@H:21]23)=[O:18])[N:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 104401Iodomethyl pivalateHCID 88669631(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-but-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 886693102,2-dimethylpropanoyloxymethyl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-but-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pivaloyloxymethyl iodide (162 mg, 0.67 mmole) was added at 0° C. to a mixture of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-1-butenyl]-3-cephem-4-carboxylic acid (197 mg, 0.45 mmole) and K2CO3 (93 mg, 0.67 mmole) in DMF (4 ml). The mixture was stirred at 0°-5° C. for 1 hour and diluted with ethyl acetate (30 ml). The dilute was washed with water and a saturated NaCl solution, dried over anhydrous MgSO4 and evaporated in vacuo. The residue was chromatographed on a silica gel column (5 g) with 1% methanol in CHCl3. The desired fractions were combined and concentrated in vacuo. The residue was dissolved in dioxane and lyophilized to afford 242 mg (97%) of the dioxane solvate of the title compound. Silica gel TLC: Rf 0.25 (1:1 CHCl3 -ethyl acetate). Estimated purity 85% (by HPLC). Mp. 90°-95° C.

Workup

  1. washThe dilute was washed with water
  2. dry with materiala saturated NaCl solution, dried over anhydrous MgSO4
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on a silica gel column (5 g) with 1% methanol in CHCl3
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in dioxane

Sources & evidence

ORD record
ord-5f8251c9a94a47d7ab00a4f81a01b251
Source dataset
uspto-grants-1987_11
Patent number
US04708955

Reaction notes

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