Sodium Chloride → HCID 86738836, compound

HRID 1702077Notes

Reaction equation

HRID 1702077 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].B(F)(F)F.CCOCC.[CH3:17][O:18][N:19]=[C:20]([C:37](=[O:40])[CH2:38][Br:39])[C:21]([NH:23][CH:24]1[C:35](=[O:36])[N:26]2[CH:27]([C:32]([OH:34])=[O:33])C(O)C[S:30][C@H:25]12)=[O:22].[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:17][O:18][N:19]=[C:20]([C:37](=[O:40])[CH2:38][Br:39])[C:21]([NH:23][CH:24]1[C:35](=[O:36])[N:26]2[CH:27]([C:32]([OH:34])=[O:33])[CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6][S:30][C@H:25]12)=[O:22]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 8000Boron trifluoride etherateHCID 867380917-(2-Methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 86738836HCID 86738836, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Acetic anhydride (22.5 ml.) and boron trifluoride etherate (7.5 ml.) were added to a stirred solution of 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer 31.8 g.) in dry tetrahydrofuran (150 ml.) at room temperature, and stirred at the same temperature for 30 minutes and at 50° C. for an hour. To the resultant solution was added a saturated aqueous solution of sodium chloride (100 ml.) and stirred for 30 minutes. Ethyl acetate (150 ml.) was added to the solution, and the ethyl acetate layer was separated, and washed with a saturated aqueous solution of sodium chloride. The aqueous layer was extracted with ethyl acetate (100 ml.). The ethyl acetate layer and the extract were combined, treated with activated charcoal and evaporated. After adding diisopropyl ether (500 ml.) to the residue, the solvent was decanted. The residue was pulverized with diisopropyl ether, and the precipitates were collected by filtration and dried to give 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-acetoxycepham-4 -carboxylic acid (syn isomer, 35.3 g.)

Workup

  1. stirringstirred for 30 minutes
  2. customthe ethyl acetate layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. extractionThe aqueous layer was extracted with ethyl acetate (100 ml.)
  5. additiontreated with activated charcoal
  6. customevaporated
  7. additionAfter adding diisopropyl ether (500 ml.) to the residue
  8. customthe solvent was decanted
  9. filtrationthe precipitates were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-17f72bbdb18343cbb82d125a7dcc142d
Source dataset
uspto-grants-1983_04
Patent number
US04379922

Reaction notes

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