Water → 2,2-dimethylpropanoyloxymethyl (6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 247030Notes

Reaction equation

HRID 247030 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:25]1[N:26]=[CH:27][S:28][CH:29]=1)\[C:5]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([O-:22])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[CH2:13][S:14][C@H:9]12)=[O:6].[Na+].[C:31]([O:37][CH2:38]I)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].O.C(OCC)(=O)C>CS(C)=O>[CH3:1][O:2]/[N:3]=[C:4](/[C:25]1[N:26]=[CH:27][S:28][CH:29]=1)\[C:5]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([O:22][CH2:38][O:37][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 104401Iodomethyl pivalateHCID 88637959sodium (6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 886381012,2-dimethylpropanoyloxymethyl (6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of sodium 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylate (0.86 g) in dimethylsulfoxide (8 ml) was added pivaloyloxymethyl iodide (0.67 g). This reaction mixture was stirred for 100 min. at room temperature, and then added to a mixture of water (86 ml) and ethyl acetate (86 ml) with stirring. The ethyl acetate layer was separated, washed twice with water, and dried over anhydrous magnesium sulfate. The ethyl acetate was evaporated under reduced pressure. Petroleum ether was added to the residue. Filtration of resulting crystals and drying thereof under reduced pressure gave the title compound (0.67 g) in crude form. This crude product was purified by chromatography on a reverse phase column (LiChroprep® RP-8) with a mobile phase consisting of water-acetonitrile-acetic acid (650:350:5), and the fractions containing the product were freeze-dried. The product thus obtained was contaminated with 2-cephem isomer.

Workup

  1. stirringwith stirring
  2. customThe ethyl acetate layer was separated
  3. washwashed twice with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe ethyl acetate was evaporated under reduced pressure
  6. additionPetroleum ether was added to the residue
  7. filtrationFiltration
  8. customof resulting crystals
  9. customdrying

Sources & evidence

ORD record
ord-68368d0b61aa42539551802a07e21919
Source dataset
uspto-grants-1987_11
Patent number
US04705784

Reaction notes

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